We have also flown in/out of TPA too. Usually it is because we are heading to Siesta Key (on west coast of FL) before/after WDW, and TPA is closer to there when flying home.
I understand flying close from home. We are less than 15 minutes from Worcester Airport, but I just couldn't bring myself to fly from there in December knowing the airport is known for weather delays. We could have booked at a great fare from there when fares were just released too! Sitting outside this summer and seeing JetBlue planes take off over my house many days (only airline out of Worcester to date is JetBlue) tends to make me second guess my decision not to fly from Worcester though!
Logan is 1 hr away, with PVD and BDL close behind at just under 1 1/4 hrs. For us, we usually leave our car in a paid lot rather than ask someone for rides, thus we normally prefer not to pay Boston's parking prices. Another issue can be the TRAFFIC! I can understand the convenience for you being close to Logan though. It sometimes is worth checking flying into MCO from PVD, as it is not that bad to leave a car in a paid lot near the airport, especially with coupons found online or AAA discounts, and fly into MCO. Another factor for us is that we usually don't rent a car for WDW portion of our trips, but sometimes TPA can be cheaper to rent a car-not always though. MCO is much better for those not wanting to rent a car due to having Magical Express at MCO.