Since your interested in a chipper...
We've got a 3pt one and for lols we hooked it up to the L2501 and it was fine with 3" stuff, getting up near / past 4 inches is about the most we were able to do with it before it ran out of power and it wasn't too happy about it. I forget the brand but I believe the PTO powers a hydraulic pump which runs everything. Something more direct gear driven wouldn't waste as much HP and should chip larger diameter limbs.
Not an issue for us, we just run it with an older larger tractor.
Most of the 6 to 8 in diameter chippers that have hydraulic feed rollers have direct drive for the chipping portion and hydraulic drive for the feed rollers.
For a chipper I want one of these or maybe one of the upgrades. Had a job to justify it and lead time was a no-go. I probably won’t worry about it until another job and have the same problem.
If you get the woodmax or another one that looks like the one you had the picture of, the only complaint I've heard about it is that the hydraulic flow control valve that they use to adjust the feed roller speed is oversized for that application, the pump puts out 4 gallons per minute and it is a 10-15 gallon per minute valve.
As a result, once you adjust the speed past about 1/3, it's at full speed.
Some people have replaced the valve with a more perfectly sized one from Surplus Center and been very happy with it.
As for tractors in general, we (my in-laws and us) have a BX2660, a B7500, a L3830 and a MX6000 (just picked up 2 weeks ago).
The BX lives with a mower or a snowblower on it.
The B mostly gets used for cleaning out the barn and tilling the garden
The L and the MX are used to cut, rake and bale hay as well as moving firewood.
Previously my in-laws my parents or us have owned a couple of older Allis tractors (WD45 was one), a Ford 8N, a Massey Industrial 35, a Case 480F, a Kubota L3650, a David Brown 880 and a Deere 880.
My thoughts:
Snowblower: Keep it to a front mount and 5HP/foot (that number is a good rough idea on PTO powered attachment size)
Loader: The MX is the first tractor we have owned with Skid Steer Quick Attach, I wouldn't have another loader tractor without one
Chipper: You will be happier with powered infeed, Hydraulic infeed is more tolerant of varying log sizes, a bigger chipper will reduce how much trimming of branches you will need to do to let them fit in.
4wd: A 4wd tractor will work circles around a much larger 2wd tractor unless you're doing something like mowing a field where traction is not a limiting factor.
Dad's 4WD Kubota L3650 was 2/3 the size and 1/2 the weight of the 2WD Massey Industrial 35 it replaced and the Kubota could outwork it any day of the week as the Massey was severely traction limited (even with loaded tires, wheel weights and a 55 gallon drum full of rocks on the 3 point).
If you want to do straight loader work, a skid steer or a mini wheel loader (look at PowerTrac if you want to go down a rabbit hole) will do circles around a tractor.
Aaron Z