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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!

However, this access point also serves as the door delivery drivers and guests use to do drop offs or walk up to knock the "front" door. 

Also, if you feel a partner who may be able to lower the interest rate is necessary to make the transaction pencil, you are dealing with too low of margins.

I have a Guest Favorite badge, Evolve is Superhost, we have around 25 reviews, total 4.95 stars.

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You can post this but you never know how guests are going to act.

If so that would make me feel better about the idea.

Do you feel it was worth the price?