Short term is managing cleaners, dealing with guests complaining about cleaners, random **** breaking, reporting damages do Airbnb, seeing a big *** party starting at your house at midnight (your property manager isn’t on call 24/7 and are charging for every hour spent), dealing with pissed off neighbors etc.You need to weigh all those costs (management + cleaners stack) minus potential high weekday vacancy minus Airbnb’s rising fees and declining service plus your time and headache spent, VS an easy / much more guaranteed paycheck.There’s a lot of guru BS in the STR game.

How much skin in the game? 

If anyone stays in past closing you hold a LARGE amount of money in escrow and charge 2x market rent.

My credit score and history is great so it’s only my income that’s holding me back, but I should be able mitigate that with a qualified co-signer if I can’t find better work. 

Is there room for a profit in this scenario or is this more of a long term game and renting the better route to take on this specific strategy? 

Investment Info:Small multi-family (2-4 units) buy & hold investment.

Let me know if you have any particular questions regarding the Milwaukee market and buy and hold.

I think it's especially important to substitute knowledge of an area with either strict numbers (that will likely keep you out of the game these days) or a solid team on the ground that knows it for you. 

Investment Info:Townhouse buy & hold investment.

Investment Info:Single-family residence buy & hold investment.