well, I can tell you this, My biggest mistake was not keeping more of the 500 or so I flipped over the last 6 7  8  years, HUGE mistake,,, so think long term, 

I can’t tell if the side wall is all windows but this will not pass for shear wall requirements if changed to habitable space.The biggest cost may be the foundation.

Probably my biggest issue right now is identifying a market where decent deals can be found. 

@Jason Regan Dealing with the city of Fitchburg is the biggest nightmare you could put yourself into.

Hey everyone, What are your biggest challenges with short-term rental investing?

Currently, they are the biggest example of hypocrisy on the planet.

Any advice on financing if they will not accept my conventional loan.I guess the biggest interest is that there is less competition and it seems like these wholesale deals are more of what I'm looking for. 

My biggest roadblock I've hit so far is figuring out who to get licensed under.

I have worked with some clients that are doing STR all across the RGV and my team and I host the biggest BP investor meet up in the RGV.

Biggest hard pass for me, I look at the partnership buying the real estate deal and how they are set up.