I can also allow a tenant to grow with me - just moved a family from a two bedroom to a three bedroom apartment.Personally the only reasons I would choose to invest in multiple markets is a) because I wanted an excuse to go somewhere regularly or b) for economic/geographic diversity.I had the advantage that my home market was good.

@Yaroslav Shtogun James gave a great explanation.

So I would suggest keeping your STR property geographically close and doing as much as possible to keep your profit% high as possible.As far as the actual house you use, I would just say - be honest, be fair and strive for the best area, most amenities, cleanest house, best communication, and any other extras you can get.

Diversifying geographically can also reduce risk and increase long-term returns.For example, there are several markets across the U.S. that are ideal for new investors because they offer affordable entry points, reliable cash flow, and strong economic fundamentals.

This is the best explanation of recapture - thank you so much!

We cover a large geographical area (nearly 400 miles) because there are usually only a few STR eligible properties for sale in any given city.  

Geographic LocationDefine the regions or markets where you want to invest.

Contractors, unless you have a working relationship with them, normally do not want you bouncing ideas off them.Understand what their hourly rate is, have a discussion with them that you are okay with paying them an hourly rate if they walk the property with you and provide you a scope of work along with an explanation of what you can/can't get away with in regards to improvements.ask them if you go with them, if they can credit you the amount that you paid.Once you develop a working relationship with a few contractors, you can bounce ideas off them and expect quality responses.I do not invest in New York.Best of luck. 

I understand Vermont has slightly more stringent regulations to contend with but it would also be closer for us geographically and thus potentially easier to manage. 

Here's a fundamental explanation to get your juices flowing:Assume a house costs $200,000 and rents for $1,500.