In Carmel, u can pay 1.5M+ for a "cottage"..

Best way to learn is to befriend an investor and over the course a million cups of coffee, ask what they wish they had done differently.My strategy is to be the second mouse that gets the cheese. :)

Closing on cottage in a resort area up north this month (area's pretty dead in the winter except for a couple of winter events). 

This discussion reminds me of the story of Paul Feldman, a cubicle-imprisoned bureaucrat in Washington DC who escaped by starting a Bagel & cream cheese /doughnut delivery service in various office buildings around and including his former employer.  

So you might look at older houses that have been broken up into a number units or a situation like a house and cottage in the backyard that you could rent out.If you wife doesn't agree to that strategy, I have been able to get started by buying "cheap" run-down houses, renovating, refinancing and turning them over to a property manager.

Kind of unique in that it seems to be a blend of "up north" woodsiness, cutsie cottageness, and waterfront recreation.

I have a duplex and two cottages in the back.

Title II is done with so-called "accredited crowdfunding" because that is the securities regime that is well-understood and that has been in place long enough for the necessary cottage industries to pop up to support it.  

Decent area, solid exterior and interior, with a finished cottage setup on 3rd floor.

"The Magic of Thinking Big"  "Go For No" "Who Moved My Cheese" are all favorites.