Good morning!

They are moving a million miles an hour and its hard for them to determine your strengths and weaknesses and how that fits into their needs. 

I got a hold of an agent early Sat morning for a listing that went live late Friday night. 

So I see my offer might be a bit weak.

They have weak contracts and leases if they have any at all.

Good Morning, Is everyone still feeling the STR market is pretty strong here or is long term rental the way to go for a single family house.

Morning all,I am a newcomer to Real Estate Investing out of the Central Virginia area.

Well the first payment of $500 was pulled this morning from my account.

I actually dumped Zillow stock and doubled down on Compass this morning.

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!