We usually agree on most topics on here, but it sounds like we have had very different experiences using buyer's agents.

sounds like you are off to a strong start. 

Hey @Jesse Kassel It sounds like you're experiencing a bit of FOMO here, especially with the number of caveats with this property.

with such a high mortgage rate, it is very hard to find cash flowing investment even at 40percent down. everyone makes it sound so easy to find something with cashflow, but its not.

Hi Sylvestre, sounds like you are doing pretty well with taking all the right steps.

It sounds to me that Kevin came into a lot of money very quick and was not prepared to handle it properly.

@Jimmy Vance sounds like overkill if they are SFR or small MFR.Only sense to do this with multimillion dollar properties.

Generally, the law requires that buildings undergo structural inspections every 10 years, once the building turns 30 years old, and that the building association proves it has adequate reserves to repair / replace anything that is flagged in inspections or projected as a needed repair in a timely manner. 

As easy as this sounds, it's not simple and usually like pulling teeth.

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!