Still on the way in, and I know better than to look back over my shoulder to see how deep I'm in, cuz it's a ways.....
If you can still look over your shoulder you aren't in very deep. Then again we have to define how the depth is calculated. Is it by the dollars spent, or the number of machines and amount of tooling you've accumulated? I've purchased almost all my machinery used, and since I happen to be in the "rust belt" prices here are considerably less than in many other parts of the country.
I have what I would consider a "reasonably well equipped" shop. There are always additional machines on my "wish list", but it's more a matter of size, energy, and availability than money. Two that come to mind are either a Moore or Pratt & Whitney Jig bore and a 3' radial drill. I passed on both a short time ago at what I would consider ridiculously low prices. A I was offered a nicely equipped Pratt & Whitney jig bore machine for $900.00, and a Fosdick radial drill for $1,100.00. Both eventually went to another "hobbyist" in the area. I say "hobbyist" but he's more of a collector. He has nearly a dozen machines in his "shop" but none are wired in or up and running. Space in my shop is now more of a premium, and at my age it's a little more difficult to transport, disassemble, and reassemble larger machines than it was 20 years ago. In this area machinery is still what I would consider "cheap" compared to the west coast and southern states, especially if you know of shops that are continually changing and upgrading to meet demand.
It might sound a bit odd, but this is the first year in a long time that I've spent the amount of time I'd like to in the shop. While the pandemic has curtailed travel and social interaction it has allowed me to complete projects I started years ago. I would estimate that I've spent 3 to 4 times as much time in the shop this past year as I have in the previous 5 years. In the past it seems there's always been far more to do outside the shop so the time in the shop has been limited.
I do still visit local used machine dealers on a regular basis, but these days it's more for accumulating metal stock and small tooling needed for a specific job. In the last couple weeks I've bought some 6061 aluminum round stock, flat stock, a hand full of reamers, and a few other small goodies I could carry in my hands. Nothing large even though there were literally hundreds of machines and thousands of pieces of tooling looking for a new home.