$2500? Yikes. That might be because of how deep it has to be due to your frost line? Bummer, it's a great convenience. For comparison sake: I hired a guy (day laborer) who helped me run a new water main from street to valve, at least 50', and paid him a couple hundred bucks. We put it 15" deep. He did the digging, I did the plumbing. I used PEX, which has a little give to it and is every easy to work with. I ran it inside some 2" PVC as a little extra gopher protection. I doubt the whole project was more than $400, including new valve and pressure reg, etc.
Would you have to blow out a fill line in winter? That might be more trouble than using a hose x-number of times in the summer. I don't know what pool owners in OH typically do about auto-fillers. Maybe not done at all? You're not that much farther north the I am...
The overflow on my pool is nice because it originates in a tank that is separate from the pool, connected via an equalizer tube, which means it's not subject to waves and splashing. But an overflow can be much simpler, and wouldn't require much excavation. Just a simple grate covering a hole in the side of your pool, a few inches below your coping, connected to a PVC pipe that runs off into your yard. It wouldn't be very deep, just below the deck, I would think. Again, something to discuss with your PB.
And just for giggles (if autofill is possible in your climate), here's a couple of crazy ideas. Install a fill line, or something like the PoolMiser, and stub out the supply pipe just enough to get out from under the new deck. So that if you happen upon a windfall, you could later spring for the connecting pipe. Once the deck is down, you won't have the option. Theoretically, you could even run the pipe out of the ground, and connect your hose to it. Is there a discrete path from a hose bib to your pool, where if you left a hose connected like that it wouldn't be too obnoxious? So you connect up a hose in the hottest months, when filling by hand is a drag, then disconnect in the winter. Then someday, run a permanent underground solution when you have the dough?
I'm only pushing this because I'm projecting. I know myself: without autofill, I'd either neglect the chore and the water would get below the skimmer opening (potentially very bad for the pump), or I'd forget the running hose and come out the next day to a full pool, a flooded yard, and/or a not-so-nice surprise on my water bill.
Just thinkin' out loud with ya...