I'm at 2200 Sq ft with 3 bedrooms, a major living room, and a climate controlled finished Florida room. 

All of the meetings that I see about ADUs are sponsored by builders who want to sell their ADUs.Are there others who want to build their own or want to share their experiences about building ADUs / converting outbuilding / navigating codes in Portland that DO NOT involve hiring one of these tiny house start-up companies?

Or until the next major recession.

Madison - strong appreciation play, but negative cash flow without a unicorn deal or major cash down. 

A majority of STR markets are relatively saturated, but that saturation is skewed towards entry level homes.

Ideally before you purchase your realtor/lender will provide you with a property management company who is willing to provide resources, leases, and whatever you need to get house hacking.

Here's a list of the best major cities for cash-flow...mostly it's the midwest and also upstate NY

I have a single family home that I've been trying to find a Property Management company to work with and I can't believe how difficult it has been.

Olympic sized pool, hot tubs, on-site restaurant, yoga, pilates, gym, steam, sauna, and management company to take care of it all.

I am by no means saying this is a bad company or even a bad investment, all I am saying is do your own due diligence - all of this information is readily available on the SEC website to review and understand what you are investing in:below is from the SEC website• The Notes are unsecured, general recourse obligations of the Company that will be repaid from the Company’s working capital.