I'm trying to convince myself that I'm not, either. What I now have has worked well for ten years, but I think I've gotten a case of "Wannabigger", and have been thinking about upsizing my X748.
My first rider mower was a '66 RF110, I found it in a yard a couple miles from my house, for $600, about 25 years ago. I kept it for 4 years; in the meantime, we moved and a neighbor at the new digs had a '72 112 that he couldn't get to run, sold it to me for $200. all it needed was a carburetor. Kept both for another year but needed something larger than either one, as my property size had increased from 1/4 acre to 4-1/2 acres. Sold them both, and at the time had no idea of the collectability of the RF, or I'd have kept it. I couldn't afford a new JD at the time, bought a Sears 18hp GT, and after a couple of years regretted it. Sold it, and bought a new GT235, which I still have. It did a remarkable job, just took longer than I wanted, and wasn't really suitable for the gardening I wanted to do, or other landscaping tasks. I found a nice Yanmar 1810D compact tractor, bought a rear finish mower, and I was much better off. The Yanmar was 23 hp and 17 pto, did okay with the 60" mower, and I had it for 6 years. I had by then bought an adjacent property and increased my mowing to over 5-1/2 acres. A friend offered to buy the Yanmar (I didn't have it up for sale), he needed something to maintain a deer plot and small cabin out in the boonies. I sold him the tractor, the finish mower, a blade and a cultivator, and bought the X748SE. A bit more power in a more compact size. Over the years I've found a few collectible JD's to restore, including the partially restored and very usable 318, which I use quite a bit to mow with when the X7 is configured for gardening or loader work.
This has got me to thinking, 'why not upsize the X7, I still have a mower(s) I can get under trees with and into the tighter spaces (318 and GT235), so find something a couple of sizes bigger than the X7 with more loader power, but still small enough to mow with?' I love the X748, it's a beast, but I'd sell or trade it if I can find a really nice 2320 with mower and loader. I can't really justify buying a new 1025R (new version of 2320) for the price difference, and a 1023 isn't enough of a move up for me. I've got my eyes on a 2007 2320 with less than 600 hrs, has a 62" deck and loader, for less than $12K. I retired last week; having the larger tractor could open me up to do some contract landscaping and garden work, I have a great pto tiller and a few other 3 pt implements. Gotta talk the wife into the trade first, though.