Your route planning looks not unreasonable for the cities you're wanting to get to.  I'll avoid the temptation to gripe about the choice of cities or the factors that did or did not go into the selection process for the list...as it's not very relevant to the discussion.
If you leave in February, it looks like you're getting up towards New England around late March or April or so.  That's an iffy time of year for the weather—it could be beautiful and warm, or it could be blizzards, possibly all in the same week.  I might suggest leaving a bit later, aiming for Boston around May.  Maybe think about swinging through the central plains cities and the Denver area ones on the way west rather than the way back to Florida, which it would be the dead of winter.  That would leave working down the west coast for the fall and winter, and a rather long final leg of the drive across the south.