I am closing in on 2 years so I will have the freedom to look for another larger live in flip if I choose or to ride it out for longer.  

The price has come down almost $200,000 dollars and it's in the neighborhood we've been wanting to raise our family, but... we'd only be able to pull in $1250 - $1500 in rent from the other unit at this location, and it would put us into even more debt.Looking for other investors thoughts on whether or not to jump at this to ride out possible inflation, or to wait and hope for a market downturn.Current Situation:Duplexmtg + tax + ins = -$1300rent = $900net = -$400Possible New Situation:Duplex (w/refinance)mtg + tax + ins = -$1900rent = $2400Housemtg + tax + ins = -$2580rent = $1250net = -$830Thanks in advance for any input you can give.

Someone with better connections than you will likely take you for a ride--push you out of the company and steal it from you, if it's worth stealing. 

It definitely was a wild ride the first month I was extremely busy and the market was competitive.

I found the houses by riding my bike in an area near me that I wanted to have the short term rentals.  

Let it ride as Airbnb and sell in 4 years. - “sell” to LLC and get investment property loan, continue to operate as Airbnb.

That said, your purchase and sales agreement can have anything in it you want so long as any terms do not violate any laws and the standard Texas real estate contract does not "over ride" your contract.

Lots of gentrifying neighborhoods so opportunity to get into a cash flow oriented area and ride the wave of it becoming more of an appreciation area as well if you get in the right spot.

I also started listening to the BP podcast on my rides to and from work again.

Don't' call it a charity-- call it what it is … "Free Rent Ride for 1 year"-- and btw the tenants and the program get  PISSED at you for not renewing , and  the charity withhold the last month rent.