I wasn't really thinking of selling initially, but a couple condos in my complex sold for over $900k, and I thought I'd take a shot to see if I could get somewhere close to that. 

I'd definitely lean on legal counsel locally to get a better idea of what options you have; you want to make sure you're not violating law by evicting a tenant for an ESA but you also want to make sure them having an ESA doesn't violate their HOA rules (sounds like it gets a bit more complex now that the HOA has gotten involved).

I ended up buying into a syndication on an apartment complex with some friends in April 2018 or so, and right after I committed to that, I had another friend call me who saw three duplexes (6 units) on craigs list.  

Almost a New owner of an apartment complex.

We haven't replaced the roof or the boiler, because they work fine, since we purchased in 2013 but they are on the older side.1) Sell As is and Move2) Develop it as there is 2000sq ft of FAR that we could build and the neighboring property which was the same foot print has already maxed out their FAR and condominiumized and sold 4 condos for about 4m.Not attracted to the condo option but it could be the only way developing the property makes sense.3) Move, Rent out both units and Hold. 4) Move, Rent it out and downsize in another area potentially upstate or a "better" neighborhood in NYCI know this is a very wide open question and alot depends on what we "want" to do.

I found a condominium unit I am interested in buying to rent out.

Usually PM companies have a realtor they work with to show the apartments at small complexes.

I own and operate all management services and invest mainly in large residential complexes and storage.

I'm trying to analyze a small apartment complex that is mom and pop owned. 18 units 9 1 bedrooms and 9 2 bedrooms. 

My father is a landlord for a 30 unit apartment complex here in Southern California and he HATES that California is a tenant friendly state!