I was in a very similar situation 8 years ago, having just moved to a place where I expected to only stay about as long as you're talking about. I went ahead and planted as much as I had space for with little or no thought about bearing age, and I'm glad I did. I might have gotten some apples my last year there except for a severe late freeze, so I never got any apples, but the trees I planted -- I only paid $3 each for fresh grafts -- were worth much more than that just as a learning experience in pruning and training. They were also a lesson in record-keeping: if I hadn't failed in keeping track of which tree was which, I would have found them a valuable source for scionwood. And if I had moved just a year earlier, I think I might still have transplanted them to my new place. There were other things that I did successfully take with me (whole blueberry bushes as well as some runners I separated, some serviceberry runners, layered figs and muscadines...) Perhaps most valuable, having apple trees led me to think about and explore fruit things further, so when I moved again I planted a lot of other/new things that I'm very glad I have now but that I probably wouldn't have planted if I hadn't already had a little experience with the more common things. So based on my experience, my recommendation would be to just plant the things that most interested me, and I think that will likely prove the most valuable (in wiser decisions about what to plant in 3-4 years, in better understanding of how to care for (and possibly propagate) what you're most interested in, in transplants/layerings/scionwood/seedlings..., etc.)

I've got some BW seedlings, started from named-variety seednuts, planted in nursery beds in spring of '98, transplanted as 2-yr bareroot seedlings in 2000 into a CRP riparian bufferstrip along the creek that borders my farm - no care whatsoever, other than bush-hogging the weeds/grass once (some years twice)a year. Several of them are producing their first crop of nuts this year. Approximately 20 ft tall. So...they're pretty well fitting into the expected 7-10 year timeframe for a seedling tree. Grafted BWs have typically produced a few nuts for me within 3 years or so.

The peach and the damson should be self-fruitful, so no need to worry about them in terms of pollination. I looked around for information regarding the Yates apple and only found the statement that this variety makes a good pollinator for other apples. So to my thinking, other apples would pollinate IT! Right? I would at least look for other late maturing apples. Winesaps come to mind, but there are plenty of others. Your local extension office might be a good place to go for information pertinent to your location. I took a couple of pome fruit courses in college but that was waaay to long ago for me to remember the ins and outs of apple pollination, lol. By the way, tree fruit varieties as old as these will no longer be patented.

I think you will find that most bare root fruit trees are at least 2 years old - they are grown on a full year after grafting to assure the graft "takes" properly. Info on Stark's website confirms they sell 2 yo trees and other sources may stretch it out another year/growing season. Generally once you get past 3 years, the trees are too large to handle easily by bare root. I'm also not sure I'd agree about determining a tree's age just by planting date. A great many trees are grown on in containers for various lengths of time and they obviously have an age to them before someone purchases them and plants them in the ground.