Sizing a tractor to the need is very important (sort of obvious). My previous 30 HP 4wd Kubota was used on my last house/property which was 2.5 acres, it was a bit overkill but completely suitable for its intended purpose. I cleared the property, dug a couple of small ponds, helped friends, etc. Fast forward to our current 30 acres. The little Kubota was way too small, open operator station (I was tired of eating dust and pollen) and the loader had limited lift capability.
My large frame compact tractor (Deere 4720) 66 HP, ~50 PTO, hydro drive, 4wd, heat/AC, top and tilt, etc. is absolutely the perfect size for my property. I don't mow more than once or twice in a year but I do use the box blade and loader/forks/grapple/bale spear quite a bit (we are a working ranch.) The 5000 series and up Deere is just too large for my needs. My brother-in-law has a 500 acre ranch and he needs a tractor in the 80-100 hp range since he uses a bat wing mower (and mows quite a bit.)
As far as resale value, if it's not important to you - that's okay with me :drink: . Resale or residual value is always an important metric for me, we depreciate all of the equipment on income taxes.