We did something similar about 18 months ago, went from 10.2 to 2023.2, staying on classic screens. We went with completely new servers with up to date Windows Server and SQL server versions which our external IT company set up, and we had an Epicor consultant advise and validate this for us.
This comment Upgrade Path - #13 by barryd covers some of the issues we had.
Overall it went well and users barely noticed as the screens look much the same. We’re now starting the journey to migrate to Kinetic browser screen by screen, we felt it too much to do all at once. We did actually introduce the new Kinetic home screen and menu with the upgrade, just so that users realised we had actually done something, and to start introducing the new UI.
We investigated cloud but decided against it primarily because of cost, but also because of some of the topics/comments here after updates make us nervous. We’ll revisit again in a couple of years.
EDIT: In terms of which version to go for, when you get to having to make the decision you could try a post like this: Whats a good version to upgrade to before migrating to browser? and see what others say. You may not want the latest release if it has particular issues that will affect your processes and there isn’t yet a patch available.