@Blair Bennett a lot of people would benefit if they sold their primary every time it gained $250-$500k

Plus have retirement and benefits.  3.  

But, if the owners have no reason or desire to sell, then you being the comps are irrelevant.I am curious, since you don't own the whole building, but are doing work to roof and common areas, that all owners benefit from, did the other two owners share in your expenses?  

I've got a multifamily building that is sitting at around $2m in capital gains. 

I'm going to be looking to get my realty license primarily to benefit my own investing ventures rather than actively looking to take on clients as a stream of income.

The seller knows the property he’s selling, and might not mind foreclosing and gaining ownership once again.  

If so, it really does open up your options as you would most benefit from a CPA who specializes in real estate.

the answer i'm giving is based on the assumption that you do not want to / can not float the negative cashflow any longer. and note: even if appreciation / debt paydown / tax benefits strongly outweighed the negative cashflow, most investors wouldn't want to / couldn't float that. so that said, i say SELL. you have just over a million dollars in equity (minus transactional costs when you sell), and you could do a 1031 exchange into a ~4 million dollar CASHFLOWING property. i invest long distance into value-add multifamily on the west side of chicago. gearing up for my next deal right now. in that price range you could easily get a value-add multifamily with potential to cashflow 15k/mo+++ (up to 40k/mo) once it reaches its full potential. it sounds like you're in markets that are probably strong for appreciation and weak for cashflow (with the long term rental strategy). if cashflow is your goal, 1031 into value-add multifamily in a higher-cashflow area. don't let having to pay commissions during the sale stop you. you're already losing so much annually; you have to stop the bleeding at some point. also note that right now, with the way these two properties are losing money, that might negatively affect your borrowing power when you go to buy the family home. feel free to dm me if i can help in any way!

Sometimes the benefit isn't juat the actual value, but the overall desireability that the amenity provides.

The one benefit is they usually leave the property in great shape!