Thanks! It's all insight I'm happy to hear.
Re: Siding - I know its not an urgent priority, but it does look like it's worse for wear. Uneven in spots, there's one panel that seems to have an issue with popping out (I'll get a picture in short order). And it just seems it was done as a bit of a hack job, lots of finishing details seem problematic at best. I'll get some pictures of what I'm talking about.
That said, I've been considering just having a company out to do some repair on the spots that are annoying, and just paint for now as you suggested; I think there's a lot of merit there.
Would you suggest just repairing the caulking, cleaning up, and re-painting the trim on the window that's got caulk issues? Seems like the lowest effort to results ratio, but I want to be sure I'm not missing something in the process.
I'm sure I'm overthinking a lot of this