Friz:
I have a 3720cab and a 2305. Both with maybe 150hrs on it but the 3720 meter lies. as the 2305 is 2.5 years older.

(The hour meter on the 3x20 and 4x20 series goes faster
than 'clock' time.)
I have the front mount Snowblower for both and next time I'll get a rear. The fronts are great for maneuverability but for the 3720 it's almost a 5K setup once you add the mounts, etc. which is insane. If I had a 4720 (or even if I did it again with the 3720) I'd either put a Rear mount blower on it, or I might put an 84 or 96" Skid steer blower with a high output PTO pump on the rear to power it. The point being to still have the loader available (or available quick). The snowblower doesn't come on/off easy enough that you'll want to swap it often.
I have 6" (each side) wheel extenders on my 3720 and they help a lot, make it a foot wider in the narrow position. (I'm 66" wide in the Narrow position with my R3's). It feels
MUCH more stable than before I had them on it.
I too would question the need for two tractors. (I use mine on different lots). Unless transport or maneuverability is an issue just get the big one. The other issue may be weight - If you have sensitive areas you'll have a lot of weight with a 3720 or a 4720 and
maybe you want to go lighter.
I run a little under 6000# when I mow on the 3720 - I drop the bucket but leave the loader on. Tractor is about 3700lbs, about 800lbs of loading in the tires, 1100 for the loader frame, etc.
I also have the 7 Iron 72" MMM deck (not the new auto-mount) AND an 84" rear pull behind for the 3720. Unless you are doing JUST mowing (or get the auto-mount deck),
taking off and putting on the 72" MMM on the 3720 is a pain in the a## and unless your doing 'girly man' tractor stuff like scooping up Bark mulch you'll bang the crap out of it doing anything. I only use it for leaf collection now. FYI on the other hand the 62D deck on the 2305 comes on and off very easily and lifts higher (Figure that one out).
They do sell front mount snowblowers that'll fit the 4720 that attach to the rear PTO but I would never get one due to them taking up more room than the tractor when I store it.
(It's a frame you drive over and hook up - longer than the tractor).
Anyway, I'd go for the 66hp 4720 in the 4x20 series if you can afford it just because...

As a sweetener the 4720 has the EPTO so you can justify the purchase by telling yourself you are saving $$$ using the PTO by running the engine at a lower RPM.

Also with all
the land you have I think you could justify the 4720.
FYI: I love my 3720 and it is absolutely unbelievable in performance and comfort. I have power to the rear, rear diverter valves, lines for a grapple hook up front, etc. - The deluxe cab is nicer than my truck. If it was highway legal and would go just a tad faster I'd be driving it to work.