The land banker, the long term landlord, the neighbor that wants to expand their home, or the horse owning owner occupant with no other options?  

As I see it, the only ways that real estate pays you well in the first 3-5 years is low to no leverage or a strategy that requires more work (short term rental, mid term rental, rent by the room, etc.).  

While I help people find their dream homes daily, my true passion lies in real estate investing and building long-term wealth.

I would like to build several (2 - 6) "shipping container" type homes for either short, mid or long term rental.

https://www.biggerpockets.com/blog/brrrr-loans-what-are-the-...Short-Term Rental Loans: What Are the Options and How Do DSCR Loans Stack Up?

And What other conditions/terms/costs do you calculate when underwriting the potential of a deal?

You would be violating Airbnb's terms of service.

I recently analyzed an asset of vacation cabins - where the seller would earn 23% ROI over a 5 year term.   

No one has ever asked me. 3) Depends on if you want longterm or short term residents. 5) We used Redstar https://www.redstarbackgrounds.com/ they give you accept/decline recommendations.

As I've come to terms with this I have taken the last five months to regroup and really think about the future which brings me to my post and what I'd like to get the communities opinion on.I successfully negotiated and acquired one of my duplexes in 2017 that I nearly have paid off (note balance is $54k, property value $230k).