I work with a ton of new investors as a realtor the #1 way to get started is just find a 2-4 unit in decent shape and buy it low down with conventional financing 5-10% then you can live in it for a year and do another next year.

The worst thing is to pay for a service where you don't get a benefit.If you have STR's and actively manage them, then there is a good chance that you can treat the propreties as active instead of passive which will allow you to offset the losses with other forms of income such as wages, interest, dividends, gains, etc.

A two bedroom 1,300 sq ft cabin is going to go for way less than a 2 bed, 2,400 sq ft cabin.One of the issues out there too is that some are setup as legal 2 bedroom cabins because of the septic but then they have lofts and such that allow you to rent them out as 3 or even four bedroom cabins to improve the rent.You mentioned one nearby you with a similar layout.

If investors want to just be lenders then I would work with them as a lender on the deal so you don't have to setup a syndication also not sure where you are located (app doesn't say) but if investors California may be way around syndicating 

Moving there initially since low down then ideally want to rent some rooms to cover mortgage!

I think @Brian G. and @Jaycee Greene hit it on the head: an event occurring/debt resetting.When the debt forcefully resets on some of these assets, valuations drop if the submarket cap rate has expanded and/or if the operator can not show a good t-3, t-6 etc due to economic vacancy and rising opex (insurance, r&m etc).If the operator can't inject equity to cover the difference, then trouble arises.

Then selling for ~ $250k-$275k?

Since then, I’ve worked as a CTO and consultant, but real estate has always been a key focus.

Live in an area for 2-3 years, self-manage the property, and then relocate again, passing the baton to a property manager.I’d love to hear advice on any of these markets for making this approach a success!

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.