Do this for as many listings as you can in your immediate area to see how frequently they are booked.

Based on the following assumptions: You can afford the monthly PITI There is a fat $ cushion The renovations are all above board The comps show that there is a large upside delta between your purchase price and market pricesYou have good creditYou have a large 6 figure amount of cash for a down paymentIn my personal case, I would actually offer a higher interest rate for a lower down payment.

However in real estate sweat equity when applied correctly can in turn lead to higher returns.

A few blips in additional costs, drop in volume, and you could lose money fast.I like businesses with fat profits off of low to medium volume.

So I guess it's what they call "fat FIRE."

Real estate in Chicago will be pretty much the same as Real Estate in Texas so learn as much as you can in your current role and leverage that knowledge to show lenders/future investors/partners why you are a good operator. 

You’ve set up some communistic straw man argument that a rich fat cat homeowner capitalist has taken advantage of poor people.

You are losing $70/month on the mortgage alone, and without knowing what else your "payment" figure includes, it could be hundreds more in PM fees, property taxes, insurance, maintenance, etc.The refi certainly seems more appealing at a glance but again, if we have to consider the additional expenses listed above you'll still end up underwater.Honestly, it seems like unloading this thing any way you can in order to limit your losses seems like the best play.

A 5-day booking scheduled to check in tomorrow just cancelled, so I'm out 5 days of revenue with almost zero hope of rebooking.While I'm all for people being responsible about their travel plans, I'm not all for hosts getting hosed - if AirBNB wants to play travel insurer, they should do it with their money, not mine.This is one of many reasons I'm glad my STRs have fat margins, because if this goes on for long there's going to be belt-tightening happening!

I definitely have some renters still paying now because they are receiving the fat unemployment checks.