I do have a 401k but I will probably do that as my last resort.

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I'm glad you've got more stable folks lined up for all the places, and I bet you'll enjoy them more anyway (as will the firethrowers, guitar players and other folks in the community).  

yes you could use rental income in this scenario if you're using conventional financing, but if you're using FHA there will be restrictions when you're using rental income to qualify while vacating/leaving your current primary residence.3) Are you trying to claim rental income while living in your current residence to buy a second home (a property acting as a second primary residence usually near a resort or vacation type area - park city, Honolulu, Miami, etc)?

One or two big players will probably take most of what you can find, even as you start getting larger numbers.

I stayed at Seascape Resort in Aptos a few months ago.

I have an acquaintance who is a pretty big player in Chicago and his napkin math showed the ROI similar to yours but we didn't have much time to talk due to the flooding and all the help my neighbors needed.   

The resort communities are generally speaking tougher to make money.

Especially with the big players. 

My brother who also invests in real esate has a place on a resort on Mille Lacs, maybe he can join to.