I was in much the same position as you recently, I had three Leupold VariX IIs on Model 70s - mine were from the early to mid 90s. I'm a banker too and understand the need to analyze/overthink.

Anyway, I had bought a 243 for the wife/kids, moved one of the old scopes over there; shipped one off to Leupold to have parallax adjusted for use on a Ruger 77/22 and sold the last one for about $100. I never stopped liking those scopes, just had use for a couple and wanted to upgrade after 20+ years. I think the most notable differences with newer Leupolds are brightness and better adjustments, and there are a lot more reticle choices.

Over the past year, I have purchased 4 Leupold VX-3 scopes, two 3.5-10x40 and two 2.5-8x36

There are a lot of people on this site that know much more about optics than me, but since my last three Leupolds served so well, I decided to go that way again. Brands fade in and out of popularity, there is always a hot new kid on the block, but Leupold has been a better one for a long, long time. As I recall, those old vari -x scopes ran about $250 new - which was a lot more money then than it is now!

None of the new scopes I bought had been mounted - they were just scopes that people had bought and kept in the box and then decided to sell. One was bought on eBay, one from the classifieds on this site, another from a similar site, and one locally. Paid about $300 for each one, except a rarer silver b&c that I had to pay more for. I think those scopes are a heck of a bargain at $300

I did spring for the Boone and Crockett reticle on a couple. We are tree challenged in ND and shots can get long. I wouldn't worry about a special reticle like that unless you may shoot 350+ yards

Honestly, I haven't been out to compare them to my old one. Click adjustments are a lot better than the old friction ones. I don't see myself getting into using the cds system, although you could buy that too, and a lot of people love it. If you are really into spinning dials there are probably a fair number of guys that may recommend something other than Leupold, but I don't know enough about it to make a recommendation. Vortex has been very popular recently, and more guys seem to be spending the big bucks for Euro glass. I haven't had much to do with Vortex and it seems like a little shine may be coming off that brand - the comments aren't all positive anymore.

From my research, I would say the preponderance of guys regularly adjusting sights/dials has been one of the biggest trends