In 2019 we nearly missed our connecting flight at Atlanta despite having 2 hrs between planes. Our flight this year to Tampa involves a 1 1/2 hr stop at Boston. Is that sufficient to land, check in and collect baggage and get to the gate.

I'm assuming your connecting flight is on a different airline? Otherwise no need to leave security. If you have precheck, you won't have a problem. If you don't, there are times of day when the lines are extremely long, so I'll put the odds at 50/50.

Don't know where you're flying from but ask to have luggages checked all the way to the final destination. You shouldn't have to pick up luggages while in transit.

Only if you're TSA pre-check.