I have done the same journey. I have a garden tractor that I decided to equip with a Johnny Products sleeve hitch, which allows me to electronically raise and lower a rear implement. (Unfortunately, it turns out my garden tractor did not have a strong enough frame to accept a Johnny Bucket.) I now also have a real tractor.
Some thoughts. If money is no object, buy the toys you want and enjoy them. However, if you need to justify the $$$, that may be difficult with just one acre. The pool infill sounds like a one-time job better hired out unless it costs the same as a tractor.
The Johnny Products implements will do more than you think. I have done many jobs with my garden tractor + sleeve hitch + box blade that folks here STILL say can't be done. Takes a bit of time because it must be done in smaller bites. When I bought the real tractor ($16.7k) I thought I would sell the garden tractor + sleeve hitch (cost around $4.5k) but find I still need it (or want it) for small quick jobs, or where I don't want to destroy or compact turf, or in tight spaces where the big tractor can't easily fit, plus it MOWS well. I have 15 acres. If I only had 1 acre I'd probably be happy with a Johnny Products - equipped garden tractor. Folks here will disagree but tractors are not the best mowers for standard, nicely landscaped lawns. I hate to take my tractor on my *lawn.*
All that being said, one of the smallest *real* tractors--LS MT125, Massey Ferguson GC1715, Mahindra eMax 20S, kubota
BX23S--are a kind of swiss-army-knife that I would enjoy having on a small property. Light and small enough to mow well (although I still think you need to remove the FEL for mowing around the house) but still capable enough to do a lot of tractor tasks. YMMV but I found the new Deere tractors inferior to other brands in every way except price. JMO, I was shopping with zero brand loyalty at the time.
Finally, I don't own the Johnny Bucket, but several years later I am very happy with the product quality and customer support from Johnny Products for my electric sleeve hitch.
Life is short. If your dream is to own a real tractor and you can afford it, do it. If you change your mind, you can always sell it.