Man you are in a great position, just the fact that your willing to move away to enhance your investing potential shows that you are hungry for it.

If you have good W2 income, check out local education / mentoring / networking groups like Wealth Club, Lifestyles Unlimited, or RICH club. 

That being said investing in rentals through a BRRRR makes much more sense for me and my lifestyle. 

But a) this is a lifestyle decision, not just a tax strategy and b) STRs may not need REPro status at all, they come with different tax strategies.

Finally, the low cost of living compared to nearby major cities and the desirable suburban lifestyle makes it an attractive option for families.3) What are some potential risks or challenges of investing in the Hartford and West Hartford real estate markets?

This was our first step into the investment world - since then several sound opportunities have been presented and acted upon - major change in our lifestyle.

21 Turnkey Real Estate Investing Passive - SFH 22 Reiology - Wholesaling 23 No Limits Real Estate Investing Podcast - Wholesaling New: "Simple Passive Cashflow" podcast - this one has a special place in my heart for passive investors ;)Commercial Podcasts (Apartment, MFH, Funding, Marketing)1 Old Capital Real Estate Investing Podcast 2 Apartment Building Investing with Michael Blank - Commercial 3 Lifestyles unlimited Commercial - Mindset 4 Family Offices - Commercial 5 CRE Radio - Commercial 6 Commercial Real Estate Investing for Dummies - Commercial 7 Commercial Real Estate Elite - CommercialAnd in case you are wondering… I do not walk around with headphones all day.

We love to get out and be active so close proximity to lifestyle activities would be ideal but not a must.

I applaud your goal of creating a passive income lifestyle.  

For down the road, might be worth at least evaluating up-front the feasibility of adding a bathroom to enhance resell.Others have said they love the 2/1's, as they're cheap relative to rents, typically are small needing less maint., and don't attract families with destructive munchkins. :)