We didn't have enough capital to get a short-term rental in our market, but the long-term market is strong here as well, so we bought our home with the intention of it becoming a long-term rental when we move out.

I have a strong private money lender overseas who wants to invest with me. 

Yes - the Multifamily DSCR Loan option is a strong option here - not sure if you've seen this BiggerPockets article on Multifamily DSCR (versus traditional MF loans) but sharing here in case it helps - https://www.biggerpockets.com/blog/multifamily-dscr-loansIs the property now fully leased out?

I would say that the most people don't discuss the importance of having strong personal finances in place before spending endless hours looking for properties.

I have a client who has 250 owner finance sfr in TX..

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!

I own a two family house in nyc that I was renting a unit to section 8.I hired a lawyer to have them removed thru the courts.I ended up signing a move out agreement which the voucher holder where she ended up staying 9 months past her move out agreement because she had her voucher terminated from having her boyfriend living in the unit when he wasn’t on the voucher.So section 8 informed me that she was terminated from the program for good only to get reinstated 7 months later.The judge ended up letting her stay until she able to reapply get approved and find another place to stay on my dime.Do I have a strong case on suing HUD for those 9 months or the city or even both?

Rent increases were hot right after the pandemic and they've cooled down slightly but I feel they are still strong relative to the increase in price for the properties.

One had a client's cold water line crack in the middle of the night and flood the basement.

It’s possible I did a poor job of explaining this, this isn’t really a service for investors per se’ in fact I would probably in an ideal enjoy doing this more for primary home buyers, this to me is an alternative to the 2.5% commission model, you cut out the most time consuming and often in my opinion least valuable part of the job which is showing people around and opening cabinets and seeing if they are soft close or not lol (I presume in this new world there will be more open house, more showings by listing agents, possibly more services that allow buyers to show themselves houses like the Redfin does on some of its listing) because of that plus the guarantee of getting at least something for your time allows you to theoretically charge much less while still providing the important parts of the job, like you should consider this area, let’s go over this home inspection repost, here’s how we should craft an offer etc, even spending time explaining rent vs buy calculation and personal finance etc, plus the being able to be paid regardless of your advice, I’ve had countless clients who has just a myriad of bad ideas I’ve talked out of, but of course you don’t get paid for that in this commission structure.