Part of the motivation for congress writing Dodd Frank was to clamp down on the investors offering preditory terms re  rent to own and seller financing and that view has carried into craigslist rent to own adds and you say zillow. 

DSCR loans are based off of down payment, credit score and either actual or market rents so it helps to supercharge an investor's real estate goals and net worth. 

It's definitely worth the trouble.

I want to rebuild but the cost will most likely exceed what it’s worth.  

As an avid public and private markets investor, I solely believe a person's network is their net worth.

I like to set up filters like "waterfront, mountain views, 20+ acres" and then coast my way around the country haha.

Check out some AirBnb monthly comps in your neighborhood to see if it is worth the upfront furnishing costs, monthly utilities and other expenses like professional cleaning and landscaping. 

I have a house where the information bubble (assessment, stats, value) is a house two blocks away, even shows a street view picture.

Additionally, do you think masterclasses or training programs are worth the investment?

If will be more work for me which I am willing to do but is it worth the headache and risk ?