We are currently living just south of Boston and are looking to purchase a 2-4 unit property in which we would live in one of the units.

Thank you for a lively debate.

Built in 1961, this residence offers 4 bedrooms and 2 bathrooms within approximately 1,500 square feet of living space.

If that is the case, then you are good to go.Next thing will be to not rent anything until you get a real live lease and rental agreements.

Lots of really good seafood and live music. 

Those can indicate poor management, deferred maintenance, difficult and expensive upkeep like ocean front which will bring up issues with rising oceans, insurance, and hurricanes. 

If you live in Texas this is a great resource to see how much MF inventory is growing in your market https://trerc.tamu.edu/data/building-permits/

There are also Zoom calls where people practice their underwriting live.

I retired in my mid-50s and live a comfortable life, grateful every day for the path I chose.Looking back, I’m forever thankful to my partner who encouraged me to take that leap of faith and move to Ohio.

Just because your guest paid one price a year or two ago doesn't mean you haven't had higher expenses or more traction in bookings to add to demand.