14-30 Day Actively Managed STR Possible for W2 Earner?

[Greg San Martin]

I own a triplex and currently occupy one of the units (I may move out). I have a sophisticated W2 from a full time job (not at home). I would like to offer actively managed STRs for a year or two until the end of bonus depreciation or longer. My structure basis was originally $0.6 mil and is currently $1.8 mil. The units have been vacant except for a few short term guests that responded to my ads late last year.

I live in a jurisdiction that effectively bans STRs that are less than 14 days. If I offer certain qualifying services, then guest stays lasting 14 to 30 days appear to remain eligible to qualify as actively managed STRs while also complying with local codes. Two loopholes may be better than one.

I am interested to hear from other owners in a similar work situation that found a way to make actively managed 14-30 day STRs work. 

What does your day look like? 

What services do you offer? 

What services do you actually end up providing? 

What professionals did you use to set up your STR business?

Why is this a good/bad idea?

If you provide STR professional services to home owners in my situation, I would be particularly interested in your thoughts. If this STR business is viable, or if there are better options for shielding W2 and rental income, I am funded and ready to roll.