For sure. We’re not saying “start fresh” just to be difficult or unhelpful. If upgrading really was the faster and easier solution, we’d help you do that.
229 items really isn’t that many in an OH system, and the vast majority of them should copy into your new installation with no changes. Your rules are the bigger issue. Again, that’d be the same no matter what you do.
Speaking to NTTRS: for almost a year you’ve left a vulnerability in Log4j2 unpatched. It’s a low risk if your server is not exposed to the Internet, but it’s still a risk. (EDIT: As Rich explains below, the risk was much greater than I recalled.) The patch was applied very quickly in OH 3, but we have no way to inform users when something like this happens. This is the best reason to keep a system up to date.
Since you’re backing up regularly, there’s no risk in updating–you can always fall back if it doesn’t work.