Don't often comment, but check in regularly. I have similar hoarding collecting interests albeit on a slightly smaller scale, Catching up on the last couple weeks worth of posts, wondering: did you make a deal for those huge PVC fittings you got at the auction? Given the retail costs they looked like a home-run.
TL/DR: Also, I know the hassles with winter well usage and tanks. All I can say is that using compressed air to push out ice blockage is kind of sketchy. Like wear safety glasses sketchy.
We use to use a similar well setup with a tank in the basement at our camp. Winter tank refills meant similar procedures. The well head was probably 700' from the house, goes under a road, and is all uphill lol. We would have to open up and walk the line very slowly, from the wellhead down to the house after refilling in below 32* temps, if you were careless, water would pool at low points and freeze, only becoming apparent the next time you wanted to refill.
After trying to free up/thaw a 5' section we found that had frozen in a low dip (and cracked/leaked) was unsuccessful, I cut the hose at the leak figuring I'd couple it. After exhausting all other options, I ended up using a compressor to push air through open ended sections from the bottom. Can't remember if I made a fitting or did the blow-gun with a rag around it. Either way, shortly after putting air to it, my buddy at the other end (200' run) started hollering. Ice was being shot out of the open end like 12 gauge slugs. Sounds funny but the force those 3" chunks of ice had with 100psi behind them is something I'll never forget.