Paul, Monogram and Revell used to mold the date of manufacture somewhere on their kits, usually someplace you could file or scrape it off. Various releases have the RELEASE date on the box- Hasagawa does that. The plans usually have the date on them, someplace. Or the copyright date.
Books on individual manufacturers also will tell you when the kit first saw the light of day.
If there are defects of some kind, or the molds are slipping, there's usually comment on magazine and on line reviews, and comments on both from us.
If you belong to a club, the members usually bring kits in to show, both built and unbuilt, and comment about the pros and cons. That way, you can see whats in the box, before you plunk down your $$.
Reviews are not the final word, but it'll help you avoid some of the not-so-obvious umpteenth reissues of a real dog.
I find that multiple buys of the same kit are usually 'cause there are a couple of schemes I (ahem) plan to do. Yeah, that's it. Rather than save one, in the hope it might be worth something more later on. Doubtful. New stuff supercedes it, tastes change.
Fresh moldings are easier to work with than the 4 millionth tired pressing.
You'll be learning by doing, like the rest of us. Asking is easier than that sinking feeling that the latest addition to the closet of shame isn't what one hoped.
A favorite story of mine: another modeler told us he was really happy when Aurora (one of the original companies, back in the OLD DAYS) had reissued one of theirs he remembered fondly from his plastic yuth. He bought one, and was sitting in his car on the parking lot, and opened it. He was REAL disappointed, and said he put it under one of the wheels, and drove over it! Nostalgia is OK, but it will only take you so far.