Eliminate debt, establish a budget, and save.

In our experience that is what carries the day along with the area and the STR restrictions or lack thereof(a whole other conversation) that deems the valuations.Airbnb and VRBO have thought of this and are way ahead of it, we scaled quickly using these platforms for two high end STR that book out great, once we established that, we created a direct book website and are slowly pulling our repeats from that.

This information can be overwhelming, but I recommend looking for the following items:Credit Score: Depending on your criteria, you may establish a minimum credit score for your tenants.

We offer DSCR loans and have an established network of appraisers in the area.

so far so good one project is well and septic.. of course we had to drill wells and do all the ground tests etc.. the other projects are basically infill with mainlines already established. out west here each state is different.. in CA you will hear the term Mello Roos ..

I recommend establishing a reserve fund for major turnover expenses, capital repairs like a roof replacement, etc.

Do I give up access to transportation, restaurants, cultural activities, doctors, emergency medical care, religious and business activities, vet care and maybe more, to live in the country on my ranch or on the beach in a beautiful country, or do I keep access to all those things and live in the city? 

Things that have stood out so far in my research: 1-Close proximity to Metro North (90 minute ride to NYC)2-Vassar Medical Center3-Marist & Vassar Colleges 4- The Walkway over the Hudson5-Restaurants/Cafes/Hotels, etc.Thanks for your time.

Eliminate debt, establish a budget, and save.

There are occasionally opportunities for grandfathering if there is evidence of legally established conversions that were done previously, but no permit records exist to show it was done.