- You can rent out the bedroom you would normally occupy.- Most cities do NOT care if an owner lives in basement, but will not allow a tenant to unless baement has legal egress window.3) Check local statutes if any limitations on how many unrelated roommates are allowed.4) Check with local building dept to see if rental inspections and corresponding requirements.5) Local statutes allow locks on bedroom doors?

STR industry led by Airbnb is a new normal just like Uber or Doordash.

Normally the manager works directly for you rather than another company.

It's normally the desire for immediate income that steers most investors towards bad investments because they are hyper focused on cash flow which is often portrayed differently in spreadsheets than in real life, and should be a consideration but not deciding factor.

Also consider tax implications of rentals w/ depreciation vs your FT job with normal W2 taxes.

My kids went through this around the same age and still have an interest.Teach him financial literacy and include him in what you are normally doing.

However going into what is normally the slow season, I am concerned about occupancy. 

Normally, they negotiate with the company and advise you on the loss. 

Otherwise they'll think "Eh, why not lease it to a 'normal' tenant?"

And yeah, 15-20% was what I was normally seeing as far as an overrun which is where the contingency came from.