Hi @Abbie Gibson, here are my thoughts on the greater Hartford (Hartford county, really) rental market in the event that you come up this far. As a licensed real estate agent myself, I can get into trouble for "steering" you to an area, so please accept these as just some generally vague thoughts based on my experience of the area and property management industry.
Windsor is a great "small town" that generates good cashflow with moderate chances of appreciation (relative to the CT Market)
Granby even a smaller town feel than Windsor, rentals are in high demand and rent prices are high. Expect high prices too, though. Appreciation likely.
Enfield is better on cashflow, but has some rough parts of town that I personally avoid (Specifically T'ville). It does have a busy shopping area, and a mall that desperately needs attention. The proximity to MA is a benefit.
Manchester strong rents, but getting into the market can be tough, as multis are priced accordingly.
West Hartford if you're in this town you're probably banking on appreciation, not cashflow.
Glastonbury Strong rents, but expensive. Multis / rentals are not common, and in demand. Appreciation likely.
East Hartford Mostly a B/C class community. I like it. Rents are strong, proximity to downtown Hartford is a major plus. Prices have gone up steadily since 2015/2016.
New Britain Still has quite a negative stigma, mostly due to crime. I hear it all the time when I'm showing tenants units in other towns and I get asked "Do you have any other units available." You can see the expressions if you say "Yes we have one in New Britain." We manage in town, but I don't feel comfortable enough to purchase in NB myself. That being said, prices can be attractive.
Bristol Strong rental market. Seems to always have demand given proximity to Hartford, Waterbury and Meriden.