Should I Stay or Should I Go? Stay, Sell, or Rent…

**Updated June 2017**  **Update August 2017**

Da na na na na na na na…

I have been grappling with a major decision since the start of this last year – Keep my place and live here, sell it, or rent it out.  What it all comes down to is exactly that – Should I stay or should I go??

A little background – I have lived in this building on and off for the past 11 years.  I have lived in 4 of the units…3 of which I owned.  I lost 2 in the market crash (as gruesome as it sounds), rented another for a year, and eventually bought the one I’m currently residing in with cash further assuring myself the bank couldn’t take this home away from me.  What I couldn’t assure in this transaction was the crazy of my neighbors, neighborhood, and this city as a whole.

I’m not sure if you’ve seen my great city spoken about in the news lately (don’t all you FI peeps avoid TV?), but Chicago is in a bit of a slump…a happiness slump.  Wop wop.  Our violent crimes are out of control and apparently, as the 3rd largest city in the states, our city is causing the overall national crime rate to rise.  Come on, Chicago!  Get your shit together!!

Regardless of all the hoopla (and gunfire), this is my city.  I was born here.  I was raised here.  I have roots here.  But things have changed.  Remember the movie Little Shop of Horrors?  Yup…those Chicago roots that I’ve nurtured since childhood have grown into a tangled mess around my neck and are slowly suffocating me – particularly the roots surrounding my neighborhood and condo.

Audrey II – not a great roommate.

It all started with the dog.  It seems in her advanced age that walking up 3 flights of stairs isn’t her cup of tea.  Me walking her before work at 3:30 am isn’t mine….but we’ve managed.

Next, it was the BF.  J lives in the burbs and I live in the city…this makes us geographically undesirable to one another.  Still, we made it work.  I spent much of my time driving to his place (the flexibility of my job is ideal) and when I couldn’t he would drive 1.5 through traffic from his work to my place…not a fun commute to see his little lady.  Sometime last winter we got busted by his dog-hating apartment complex for bringing Bubs, prompting J to continue the 1.5-hour drive to and from work several times a week.  Thankfully, this July he moved into a new dog-friendly apartment…with a yard…and free laundry!!

Needless to say, we have been spending a majority of our time at the new digs.  But, not all of our time.  When J’s kids come over (he has joint custody) I head back to the city, Bubs in tow, and fiddle around my house for the night then head back to the burbs (I pretty much live there now, though all my belongings are still in the city).  If I’m not going back and forth there, I am at work flying to and fro.  The whole thing has gotten me so turned around I don’t really know where I belong anymore.  Similar to the chick looking for its mother, I am constantly walking around asking “Is this my home??”.

Image result for are you my mother

Which brings me to my last point.  The building I live in.  I love it.  I’ve loved it since the first day I walked into the grand marble entryway (apparently the 2nd largest in the country at the time it was built around 1912).  But things here have changed.

The area is no longer as safe as it once was.  We have a gang war happening just a few blocks North of ours.  There have been shootings in front of the school across the street.  Homeless camps are set up under the viaducts off LSD.  My car was stolen from across the street and was missing for 3 months before being recovered.  And, the more recent discovery, I have a crazy neighbor directly across from my window who has taken to throwing ashtrays through my windows and waving machetes at passersby on the street.  When you don’t feel safe in your own home, the walls tend to close in very quickly.

Image result for walls closing in gif

Those are the downsides and believe me, I know they could be waaaay worse. I have a roof over my head, running water I can make hot or cold, a fridge (sometimes I even have food in it!), AC, cable/internet, and 8 coin operated washers and dryers at my disposal.  I am not complaining (well, maybe a little), I am just making the pros and cons bullet points so we can figure this out.  So, let’s compare them to the upsides…

My place in the city is cute and quiet.  It is walking distance to the lake, bike path, grocery stores (even Aldi!), Target, restaurants, bars, public transportation.  The location (minus the proximity to gangs) is ideal.  Shit, the street parking isn’t even permit!  The best part about it??  My place is DIRT CHEAP!

I pay $266.36/month for taxes, assessments, and insurance.  I bought my unit in cash October 2014 for 65K.  Yes, it was a steal…but one I’ve paid generously for in past transactions (more on that disastrous adventure HERE).  Question is does the tiny price tag make up the sacrifice of being a prisoner in my own home…or the fact that I only use it on average 5-6 (more like 1) days a month?

So back to the original question.  Should I stay or should I go?  If I go there will be trouble and if I stay it will be double…  Here are my options:

1. If I sell, I’ll have to rent/buy somewhere else (most likely the burbs) causing my cost of living to skyrocket…goodbye 75% savings rate!!  Units are currently selling for 90k.  Also, I’m paying rent with my BF now so my savings rate has dropped though not as much if I was living on my own.  In a living arrangement such as mine (did I mention I live with 2 teenage boys??), I  kind of like the idea of keeping my place as a fallback just in case…

2.  If I stay, I can continue my cheap city hermit lifestyle…and possibly be shot while walking the dog or killed by a machete in my own hallway.  This option took care of itself due to the above, however, if something changed between my BF and I would I want to move back to this apartment?  I still have Bubs who is not fond of the stairs and probably more so now that she is older.  Also, in my advancing age 😉 , I am not a fan of the 5 month winters and brutally hot summers.  I would prefer a milder climate where I could be more active plus it’s helpful that I have quite a few friends in other climate-friendly SWA bases that would love for me to grace them with my presence.  So the answer to #2 is a no – I wouldn’t move back into this unit.  Staying is not an option.

3. Last but not least, RENT MY PLACE OUT and create a new stream of income.  I have been a landlord before so that part doesn’t bother me.  I can easily rent my place for $800 on the low-end which would equal a monthly surplus of $500+…yum! 

Two caveats to renting:

  1. I am currently #4 on the wait list (now #2! I’m set to rent!).  Three rental unit has to sell before I can rent mine out…that may take some time.
  2. The moral dilemma of putting someone in my unit when I myself am afraid to live here.  I guess that is relative to wherever my new tenant would have lived before…but still, something to think about. (It has been months without an incident within the building minus a storage unit robbery but summer usually brings an uptick in gang activity so fingers crossed they have settled their war.)
  3. I’m over the moral dilemma and on to renting this sucker out.  Turns out my earlier assessment of $800 a month was quite low and, in fact, I can rent it for $1000.  🙂

So we are down to 2 options… Should I Sell or Rent?? I am steering towards renting it out.  I truly love my unit and the area.  I have high hopes the gangs will eventually get priced out of the area which would make it safer plus we all know Bubs won’t live forever (please don’t tell her I ever said that!!).  This would be a lovely place to keep since my family is all here…  but the fucking weather!!  I suppose global warming might take care of that in due time as well.  Ugh…

Of course, I could do nothing (as I’ve been doing since the beginning of the last year) and wait to see what happens with the neighbor, rental list, and sales prices in the area.  Shit!  I just talked myself right back to where we started…  August Update – I am #1 on the rental list, moving back to the city for a month to sell my furniture and pack my belongings, and will begin showing the place next week.  More info on this all came about HERE.  🙂

** What would you do??  Have you been in a similar situation?  I could definitely use a bit of counseling…  If you have any suggestions feel free to email me or shoot me (not literally, please) a comment in the box below.  🙂 **

Until next time…

6 thoughts on “Should I Stay or Should I Go? Stay, Sell, or Rent…

  1. Sounds like you have a few separate decisions that you might be rolling into one.

    #1 – where do you want to live? Follow the happy. Has little to do with selling or holding your property.

    #2 – what are the investment prospects for your flat? You mention it is rentable, maybe in line for some capital growth. If the return prospects beat alternative investments then hold it, if not sell it (opportunity cost… just don’t forget to factor in the transaction costs, they can be brutal).

    #3 – are you willing/able to afford to hold it until you could rent it out? If no then that answers #2!

    #4 – if you sold what would you do with your newfound wealth? Buy elsewhere, rent and invest? If so invest in what? Etc

    The good news is as you don’t want to live there again it is now just an investment, so let the numbers decide.

    Good luck


    1. Hi Slow Dad! Thanks for the awesome response! I am usually quite swift at making these decisions but there are so many factors that I appreciate talking this one out.

      I’ve always been a gypsy so I am pretty quick to adjust to wherever I live. I currently live with my BF and his kids which works well and we have plans to eventually move to a better climate once the youngest is out of school (4 more years). That is my primary reason for staying at the moment.
      It is rentable as soon as I hit #1 on the list. Apparently there will be a unit moving out in the next month so I need to make this decision quick. If I become #1 I only have 2 months to get a renter (completely doable) before I move to the bottom of the very long list again. If that happened I would sell in a heartbeat.
      I can afford to wait it out indefinitely. It costs a small fraction of my income to keep it active.
      If I sell I will throw it all in VTSAX for now. In any area I would like to live the housing markets are experiencing massive inflation. Great if you already live there, not great if you are just trying to get in. For now, I have a home with my BF and he is firm on never owning again which takes care of that!

      I think waiting to see what happens in the next month with this supposed unit opening up is key. But I need to establish a sell by date. I don’t want to go into another winter in limbo or try to get it rented in December in Chicago. Not a great market then! 😉

      Thanks for chatting it out with me!! I’ll revisit this next month…again!


  2. If you sold, what would you do with the proceeds? I guess that’s one of the most important questions in your three potential choices. What you do with that freed up cash could be a big factor in which would be the best financial decision.

    Although, I think with a situation like this some of it needs to be emotionally made – if you don’t feel safe in your own home it’s definitely time to pull the plug even if that means losing a bit of money or potential growth.

    I’d say renting it out maybe – if you just can’t bare to part with it. But it sounds to me you’re realistically only left with 2 options – rent it out or sell. You only live once, you can’t live with such unhappiness. Money is a tool to bring you comfort, necessities safety and aid in happiness. It’s a pretty worthless thing to have if it isn’t aiding your life – might as well use it to get to a safer/happier place.



    1. So true, Jasmin. When I first moved to this building I loved it and the area…but a lot has changed in the past 10 years. I think renting it is the best option. To sell makes no sense when I only purchased it two years ago. The price was once 100k and I think it will get back there in a few years. If I sold I can’t buy for another year anyway so the money would just be sitting or put into VTSAX…

      So I’m declaring the decision made. Rent it for one year and then revisit my options. By then I can buy something else or just hang on to it.

      Thanks for your input!! 🙂 It always helps to be able to bounce these questions off others. I’m waaaay too close to the situation.

      Liked by 1 person

  3. hmm, tough one. I don’t know anything about real estate so it might be beneficial to talk to someone who does. Personally I need to love my neighborhood, and I would hate to feel like a prisoner. I would consider selling or renting it out, even if you have to wait to do so. You should’t feel guilty if someone lives there. It’s their choice if they are aware of the violence nearby. BTW that makes me sad to hear. I grew up idolizing Chicago as a Detroit kid. It seemed they had their sh*t together compared to us.


    1. Right?! So tough! I was a Realtor for quite some time and always bought my properties with the intention to eventually make them income properties (I got bit hard in the crash). This one was no exception but given the recent events I felt that moral pull…but you’re totally right! Perhaps it is a step up from where they came from! 🙂

      Detroit, huh? We grew up practically neighbors! If you ever find yourself in Chicago I promise to show you the best our city has to offer…minus the bad. 😉


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