Sad but I can't really think of 10... my progression would probably be
1.) PA-28-181, late 80s model with some nice upgrades like a 650, don't need any real glass though. Would be an okay cross country plane and a cheap way to build time
2.) SR20, would be a nice comfortable upgrade from the Archer, with some speed advantage.. without too much of a leap to turbos, FIKI, etc. and a fairly mild learning/adjustment curve
3.) Diamond DA62. I would skip the SR22 altogether and go for the twin. The DA62 has FIKI, has redundancy of a second engine, is modern and comfortable (like a Cirrus), and doesn't rely on some rube goldberg ancient avgas engine tech, but would be running JETA with FADEC engines, and give me a lot of payload options depending on fuel load, etc. For the typical 3 hr mission I could easily load up a DA62
But then I have to ask myself... if I can afford a new DA62, and not just afford to buy, but actually own, operate, and maintain it, then why not stretch the budget a little and just get a TBM.. or even something like a Mustang? The only reason to stay non turbine would be to fly into some smaller airports? I don't think I've ever seen a turbine at Catalina or Big Bear or Montauk for example (but I'm probably wrong)