Just how would you be using a tractor?
Case and Ingersoll are the only tractors I have much experience with but some things to consider:
Same technology since the 70's -only somewhat true. True for frames just as it is for all other brands if the design is good. Somewhat true for style but that's rather superficial. Not true for engines which are current for given era. True for drivetrain but only because the technology itself is unchanged. Power steering is available, electric PTO is standard. No cup holders.
Parts - Prices high? The parts I have needed were reasonable t high, availability very good. Even parts for old Case's are still available from Ingersoll dealers as well as salvage yards and e-bay. Many parts are available from OEM suppliers. For example, the dipstick mentioned would be available from the Onan or Kohler dealer for less money than paid at the Ingersoll dealer. Examples - new clutch wear disk $17, new skid shoes for snowblower $30/pr. I haven't needed any non-consumable items so far, that is, in 7 years I haven't broken anything yet.
Dealer support - find your own comfort zone (I once couldn't find a Toro dealer near me). My dealer is 30 miles away. Sometimes I drive up there, but there are dealers who sell parts on the internet. For tune-ups I use a mom-and-pop shop.
Prices - New 18 HP Ingersoll tractors sell for $5700 with 48 inch mower or snowblower on sale. Add a thou to get both attachments.
Performance - The Ingersoll hydraulic drive is unique. I don't know how durable the hydrostatic units are in other GT's, but in the Ingersoll pulling heavy loads is absolutely not an issue. It's the only drive system with the variable speed of hydrostatic with the durability of a gear drive. Ingersoll does not have a mechanical drive to a hydrostatic unit with its own internal pump. Rather, the engine drives a hydraulic pump and connection to the drive motor is hydraulic only. No one else has it. Wait - I believe the ZTR mowers use the same principle which makes the Ingersoll technology more up-to-date in a way.
Durability: Ingersoll tractors are built like commercial or industrial equipment. Cast iron rear axle. Nothing else like it.
And almost no plastic anywhere.
Long attachment list. Including some unique to Ingersoll like the wood splitter. You probably know about them already.
Extra hydraulic power. Because the primary drive is hydraulic there is lots of power to drive attachments that use hydraulic power.
The fact that the attachments transfer year to year is very handy when shopping new or used. Lots of stuff out there changing hands. Implements are overbuilt just as the tractors are.
I believe but cannot verify that the hydraulic drive provides hydraulic braking when going downhill that others don't have.
Ingersoll is American made.
There are some Ingersoll forums. tractorforums dot com is one and a real active one is in Yahoo groups (casegardentractors).
My collection is a Case 446 (16 HP Onan, 44in mower, 48in snow blower, sleeve hitch, box scraper) Ingersoll 3010 (10 HP Kohler, 38in mower, 54in dozer blade) Case 646 (that's a purpose-built FEL with 16.5 HP Onan). I have $4900 invested in the whole works, and bought different items at different times, and mixed and matched tractors with implements.
My point is that you could do very well with a used Ingersoll. There are a couple of 20HP units for sale in my area in the $2500 range with 60" mower and snow blower or blade. Hours in the 800-900 area.
I agree the belly mower is too hard to remove. I'm thinking of hoisting the front end of the tractor with a chainfall to attach/remove the mower and that would make it as easy as anybody's. The other attachments are already easy to hook up in my opinion.
Hope this helps.