We currently have a 22.5' HTT and have a 27.5' Outback Terrain 250TRS TT on order. We did not want to go that long mostly for taking up room in the driveway and for getting it into our favorite type of camping spots. Time will tell but in the long run I believe we will be glad we went 5' bigger.
Floorplan- New TT is going to be way better
Finances - we can swing it at this point so.. Hard to justify the money but watching the kids making lifetime memories is priceless. It don't get any better than sitting around the fire relaxing with family and friends. Sleeping in your own bed instead of one at a hotel that who know who or what was in it last night - no brainer!!
Tow Vehicle - Tow capacity should be good but need to watch the cargo limit.