I assume you are probably losing a few of those bedrooms for living rooms, kitchens,  hallways, stairways etc. if converted from 2 to 3 units.  

I would like to group both of these properties in some sort of limited liability corporation, but I think I lose my tax exemption once it's in the LLC.

If I am losing money on LMHA as a landlord then there should be 10x that number of good people losing their vouchers because they cannot stay in good standing with the excess failures the system has at present. 

And in fairness, not worth doing if you're not making more than that anyway.If he does something like this and it exceeds the SGA (Substantial Gainful Activity) limit he would lose his disability right? 

just don't do a lease. as others have mentioned, this forces the buyer of the property to take over the lease (if its even allowed/ they qualify) and it certainly does make the property a little tougher to sell. i'm also doing a house hack, and here in CA, its made a world of difference for me. the bulk of our energy usage is in the summer when we want to run the a/c. my bill stays a constant $228/mo (i pocketed the tax credit and simply financed the panels after that grace period). instead of getting an $800 bill in the summer months, we run the a/c at a constant temperature 24/7 on auto, stay comfortable, and i typically get a little bit coming back at the end of the year. don't expect to pocket this "little bit back" by being conservative with your useage, it sort of is a use-it-or-lose-it situation... i think i got $54 back this year.

The man selling said he knows he will lose money on the deal as the property already appraised for $560,000 but would love to get a young investor like myself into the game since his son did not end up sticking with it.

Good quality of life, good potential for appreciation over time, and an area that is unlikely to lose its draw for young professionals and college students for future tenants.

As an agent with a team we can't work on deals much under 200k without losing money.

Hey @Kyle Jacques, so leaving Evolve does mean, like @Patricia Andriolo-Bull said, you lose the account and will have to start from scratch.

Quote from @Jose Remor: Yes, you can save $500 by managing yourself, but you can also lose a lot more than that with some rookie management mistakes.