I think if anyone chose to focus on inbound crews and create parking like you said, as well as crew amenities (large dining areas, etc), they would be booked year-round and in-demand.

Another option if you're looking for something with higher yield than index funds, that's hands off, and will teach you a lot about real estate investing without having to do it yourself could be investing in syndications which is referred to in the book Jonathan recommended.

Depending on local regulations, you can mix up STR/MTR/LTR. 2) Get systems in place in those exact cities; 2 PMs preferably via NARPM, 2 high quality inspectors, and rotating book of handyman, 1 lawyer, and a credit union contact for leverage along with investor friendly nationwide lenders.

I also know a few property managers I can recommend who are responsive and experienced with investors.Let me know when you finalize your travel dates—I’d love to meet up while you’re in town and show you a few options!

. - The ultimate house hack, live in the small ADU unit and rent out the two levels of the main house on AirBnb in San Francisco (I would have thought STRs are oversaturated in S.F. but it worked for them and they stay fully booked).

There is a BP book by Heather Blankenship that would be a good place to start - Real Estate Campgrounds.

I have three listings, 1. unit with a pool and hot tub, 2. unit with a hot tub, 3. both units together as a 12 sleeper.Gross monthly income (after booking channel fees) for the first unit over a 7 month period was $7309.Gross monthly income for both units over a 14 month period is $11,297 (after booking channel fees) As a long term rental the combined rent would be in the region of $5500.Is it possible to sell the property based on the income generated by the STR business or would the value always be based on bricks and mortar comps? 

@Alex Hymanson  you should read the book...Storing Up Profits. 

Then you can read a more in-depth book like The Book On Rental Property Investing by Brandon Turner or The Unofficial Guide to Real Estate Investing by Spencer Strauss.2.

@Luke H.Hi Luke,  As a private money lender myself I will focus on one element of your deal---5 years is a long time to be finally paid.