upgrading from monterey which os is the best?

Not sure whether to upgrade step by step through each OS since Monterey.

What kinds of issues are there with subsequent OSs?

Have a 2019 MacBook Pro 16" currently running 12.7.6.

Use Office for Mac.

Don't think this matters but I also have Parallels & Windows 10 to run Quicken Classic Business & Personal. This runs a virtual machine (I think that's the correct terminology).

I am always reluctant to update when something is working for me - as evidenced by how far behind I am.

BUT realize this comes with it's own set of potential problems, thus my question.

Thanks to anyone who is willing to give me their thoughts, appreciate your time.