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

Da na na na na na na na…

I have been grappling with a major decision since the start of this 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, 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 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.  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).  And I still love it.  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.  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 dirt cheap.  That’s it.  The only upside amongst a slew of bullshit downsides.

 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 in a different post).  But, again, is the price worth the sacrifice of being a prisoner in my own home…or the fact that I only use it on average 5-6 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…  Or maybe that’s reverse in my case??

1. 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.

2. If I sell, I’ll have to rent somewhere else (most likely the burbs) causing my cost of living to sky rocket…goodbye 75% savings rate!!  

3. And then there is the third option – RENT MY PLACE OUT and create a new stream of income.  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 #4 on the wait list.  Three rental units have 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.

Of course, I could do nothing (as I’ve been doing since the beginning of the year) and wait to see what happens with the neighbor, rental list, and sales prices in the area.  Ugh…I just talked myself right back to where we started…

** So what would you do??  Have you been in a similar situation?  I could definitely use a bit of counseling on the situation…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…


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

  1. 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. 😉


  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

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