Yup, I'd do two stops. We fly out of Bangor, ME, and the options of a direct flight to ANYWHERE are minimal, and certainly not to Orlando. For our upcoming trip (8/17-8/26) DD and I are flying out of Bangor at 6am, with stops in LGA and ATL, before arriving at MCO at 2:15. I know I am taking my chances, but we roll the dice every day. This itinerary lets me leave early in the morning from my home airport where DH can drop us off, rather than leaving at 2:30 am for the drive to Portland and paying $120 in airport parking. Can't go anywhere without one changeover anyhow, so it's no big deal. I will pack travel size makeup and toothpaste in our carry-ons along with a change of shirt and undies. That'll hold us for a day if the bags get misdirected, but with more than an hour on the ground in each location, the bags should make it also!
To me, it's worth the money saved and convenience of leaving from home to take the flight with the three legs. Only you can decide!
(and yes, I know Allegiant flies from Bangor. Flight days are limited, and not cheap... $140 each way plus taxes, and only to Sanford, so no DME. Not a good option for us this time)