We do have a garden shed at the moment ... maybe this can be replaced with a small ADU.

Frankly I would not even entertain the idea of an eviction at the moment because of the challenges so you should just screen the property well and/or get the units vacant as is. https://www.mass.gov/guides/the-attorney-generals-guide-to-landlord-and-tenant-rightsFull eviction moratorium here: https://masslandlords.net/massachusetts-eviction-moratorium-full-explanation-and-faq/https://www.mass.gov/lists/moratorium-on-evictions-and-foreclosures-forms-and-other-resources

At the moment, I'm losing about a hundred a month on it, which makes me think if I should sell it next summer when the current lease with my tenant is over or if I should keep it as rental for now and sell in a few years with a profit (hopefully).Here are a few things to consider:- I can potentially break even on this rental if and when I refinance (not taking rental expenses into consideration though, just the mortgage could be covered by the rental income)- There is a proposed apartment community to be built right across the street from my condo - twelve 3-story buildings of studio and 1 and 2-bedroom apartments, with 25% of them being set aside as affordable housing.

It took literally 1 year and 1 month to remove the tenant from the moment we filed the unlawful detainer (we filed this ourselves before hiring an attorney) through jury trial (the owner can represent themselves during these proceedings up until it goes to jury trial, that's when we had to hire an attorney) and finally the Sheriff's lockout.  

At the moment I am a class A CDL drive that hauls construction equipment to commercial and residential job sites.

I'd be tempted, but that $51k is a bit steep for me at the moment.

My wife and I are DIY rehabbing our 4 bedroom Fishtown shell at the moment.

At the moment I want to just chat with a CPA about structuring everything for the best tax benefits.

At the moment, given my credit score and income, it looks like I'll be able to take out about 200k.

That'll allow for many years of failures and teaching moments that will get worked out with time.