Then again, it's not just Boston. They have the same standard in Orlando from my experience.
If you pack the stuff you need right away in the first carry-on and check the second, DME will get it to your room within a couple of hours of arrival, so no big deal there. You say you want to save yourself hassles, checking one of the bags (curbside check-in reduces hassles, big-time) with DME tags on it, should reduce your hassles; it has been my experience that two carry-on bags are somewhat difficult to manoeuvre anyway, so letting DME take care of one of your bags might not be a bad idea.
Have a great trip.