…Neither of those time periods are cushy. The Old Republic is a constant war between the Sith Empire and Republic, reaching far into the core worlds. I wouldn’t call that cushy for the average dude. You’re either enslaved by the Sith, enslaved by the Hutts, or conscripted by the Republic.
Post-OT in Legends wasn’t exactly nice either, what with the Yuuzhan Vong War which killed an estimated 300 trillion people and multiple planets completely destroyed. You’d actually be better off in the Galactic Civil War! At least then only one planet blew up.
Why would you want to though? I can understand the retro market because there is software like games that either won’t run very well, or won’t run at all on modern hardware. I’m in the market for a ‘powerful’ machine circa 2003-2005 for that exact reason.
When it comes to machines made in 2015? I’m not sure there’s a lot you can run on those machines that you couldn’t on modern hardware, apart from Windows 11.
I guess you could use them for things like media servers, but it would have to be phenomenally cheap, as in cheaper than cheap modern hardware.
Personally, my rule is a 10 year gap is old, a 20 year gap is retro.