Overkill? Naaaa... You are no where overkill with what you listed... the biggest machine you hit on was a tc33d or similar model... You are talking pto hp in the mid 20's.
If you want that 5' rotary cutter.. I would imagine you want around 25 pto hp... might get by with that tc29... If you go to a 4' cutter, the tc 24 isn't bad.... all are ok for the other taskes.. like loader, snow and driveway maint.
If you want just big enough for the 5' hog.. I'd guess the tc29.. just don't think you are gonna mow 3' heavy wet grass at 2" sapplings with it in 3rd range, taking a whole swath at a time...
Overkill is hard to figure... I started w/ 3 ac, and wanted a compact tractor like a tc18.. when i went to the NH dealer, I instead picked up a used beefy NH 1920 for the same money practically as a new tc18 with some options... same money.. just 33hp vs 18 hp.. etc... glad i did, as I picked up 10 more acres the next year.
Naa.. overkill is looking at a ford 8000 ( 105 PTO hp ) and having 13 ac... ( there is a guy down the road selling one in great condition for elcheapo.. .. those big ag tractors just don't hold value against compacts.. etc... )
Soundguy