The process seems daunting and overwhelming, and I am not confident I will put the time in to talk to sources, analyze, and find properties for investing purposes. 

For tax purposes, rental income is generally recognized in the year you receive it, not when it is paid.

In addition to STR'ing the main house, he is building 2 more units (ADUs) on the back side of the property.

The main thing I see when coming across this is deferred maintenance.

I would probably market it more for events, but use VRBO for that purpose.   

The hilly terrain is a main reason for this and you can't really see that on a map so knowing the areas is key.We have old housing stock as well so big things like plumbing and electrical can vary cost wise if they have or haven't been updated.

A goal gives you direction, purpose, and excitement for the future.

The only thing we cover is main components, HVAC, roof, siding etc..

The main issue is your exit is capped so if your costs go up, your profit goes down.

My main goals with these initial projects are:1.Gaining valuable insights into the local market.2.Getting hands-on experience with out-of-state investing, particularly when it comes to remodels and managing from afar.3.Testing the entire BRRRR process to see if it’s the right strategy for me long-term.If all goes well, I’d love to scale up and explore multi-family projects.