I’m reading the multifamily millionaire volume II book (I did read volume I).  

I've been in the Hawaii flip scene for about a decade.

It does seem to make some sense to keep living there with the help of a roommate paying the mortgage.

I love the concept. 

The key to success lies in ensuring you're entering the market at the right value.

To me that reeks of someone that wants to do STR (which you do), but is trying to hid that fact behind a term that doesn't indicate what's being requested.To me, a "corporate lease" would mean someone wants to lease a unit for their business and put it under a company name, and not someone that's trying to lease to STR visitors.I need to make a cut-and-paste reply to this question like that dude who literally replies with a mile long message to everyone that asks about LLC.   

I was able to see those for you here https://www.biggerpockets.com/analysis/rentals If you can't see those feel free to email [email protected] with your browser and a bit more information about where you are seeing the issue

The slowest months of the year are typically October - December.

Quote from @Karl Kauper: The tenant should figure his own life out.

It will depend on the quality you're looking for..