I recently started using DoorLoop to manage the 87 doors in my property management firm, which are owned by 16 different owners.The website and features feel unnecessarily complicated, despite the attractive interface.

Thanks Mike - unfortunately my custodian doesn't seem all that "user friendly".

It’s going to be hard for you to “get a good deal” without screwing your friend. 

I'd recommend you not just look for an investor-friendly agent, as there are a lot of those, but look for a realtor that knows Airbnb.

But I just spoke with a friend who has an STR equally far away and his CPA approved material participation.

How exactly do you find out if municipalities are friendly or not? 

Rightnow, trying out Waveapps.com as its free and simple interface. 

A lot of his friends think that getting a "real job" or creating a "real business" is for chumps.

DealCheck - Clean interface, free tier available.

Something with a simple interface and low learning curve.