If you see REI for what it is (yes the ability to make money, but not in every investment) and realize that there is more to life than money (though I'm happy to have some and the options that it provides) it should help with keeping things in perspective and you'll enjoy the ride a lot more.

 $96,000 loss on $250,000 investment, not including opportunity loss of riding up $250,000 for three years.  

Can you always get ride of it for what you have into it? 

I started looking at Ridgewood because I could ride into midtown on the M train without transfers and it's a very safe neighborhood that has experienced a lot of interesting growth recently.

Right off I495 so actually should be a pretty easy ride for you.

Last year in 2020 it was a rough ride for the short term rental market especially in Orlando.

You will find out sooner or later if shes willing to trust you and ride it out.

In my opinion, no, if they are paying the rent and not complaining about everything underneath the sun then let it ride.

I'm not saying Cleveland is a bad place to invest, especially if you are at the end of your investment lifecycle and are looking for a safe place to park your money and ride out retirement, but as I am a 30's something male I wouldn't want to invest there in the hopes of growing a future.You look like a young guy, so I would advise picking a location with good future growth, and worry slightly less with the immediate cashflow situation. 

Have family in arizona, they hunkered down during the crash, I suggested they double down and ride it back up...they just rode it out and probably are wishing they had taken my suggestion.