I think the main difference is you can start small and scale most business you would start take more capital and could be a tad more complicated than buy house rent house. 

I doubt that this would create additional legal complications, but I cannot have a valid opinion on legal matters, not being an attorney.

Expectations get very complicated in Partnerships and the value add of having partners gets watered down with that many people. that being said, I would wait for partnership stuff until you have a house.

How complicated is the evicting process?

Luckily being in Boulder I’m sure you’re surrounded by qualified CPA’s and if that’s the only “complicated” part of your taxes I’m sure most could help. 

The whole issue of "does gross income include cleaner fees" is further complicated by the fact that from a TAX perspective, it absolutely is income. 

@Diana J AdamsOne technique you may want to consider if you are self-managing is paying attention to local area codes used by guests coupled with a .edu email address.

RULE Always don't complicate a house hack

It's a complicated manuever, way more so than a simple reverse because a NNN lease cannot be used to give you control of the property. 

Wholesaling combined all the difficult parts of real estate, lead generation, marketing, sales, contract knowledge, construction knowledge, ARV knowledge, etc etc... personally I see wholesaling as an advanced technique yet most start there.You can try and get contractors to give you bids, but that will get old quick after giving you 10-15-20 bids and seeing $0 return.