However, I live close-by (30 minute drive), recently retired from my day-job, and if the loan is not too large, I might be willing to do a deal just to learn a bit more about another side of RE.  

I suggest that you make it a point of finding a good lender, not just someone who can do the job of helping your clients buy their home but someone who is willing to teach you.

I've never really done a deep dive in analyzing the area because it is a retirement community, median income is very low, and there arent a lot of jobs in the area.

Changing jobs!

Just use google maps and you can do a good job counting the number and size of units.  

If you believe you can carry this place, without a negative carry, make any necessary repairs and can make changes to improve the rents...

There are a couple of unique tax laws to real estate investors - 1031 exchange, bonus depreciation on certain improvements, Qualified Opportunity Zones, real estate professional status, etc.Make sure that the accountant you interview to understand the above concepts.best of luck!

@Brittany MyrickIf I were getting started in real estate investing in New England, I’d focus on researching local market trends, especially job growth, rental demand, and the broader economic outlook.

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

Plan to make some tenant improvements to push rents closer to market rate for the area.