Thinking of picking up my first property in western MA soon.

Determining whether to do a cost segregation study or not has a lot variables.

For a senior to qualify for Medicaid, there is a 5-year "look-back" period for determining their assets. 

You need to learn how to analyze property and determine if they are a good investment.Here's a guide that describes how to analyze a property.https://www.biggerpockets.com/blog/rental-property-cash-flow...

How would I determine which is best for me?

I am interested in flipping in the downtown / Patty Jewett area and would love to get connected with someone who flips in the Springs (and hopefully pick their brain a bit).

Determine Your BudgetSet a Realistic Budget: Consider the cost of tuition, living expenses, and your financial situation.Mortgage vs.

Determine what type of property you want to buy - What Zip code, what condition homes, price range, etc.Contact 3-4 realtors that helped buyer agent buy the type of homes you are looking to buy.Then go with the 1 realtor that you connected with the most.

Did you run a DSCR calculation to determine cashflow?

I had one that I was able to pick up last year.