One mistake I
didn't make was to start with models or vintages of guns that are in the higher end market. The potential for a financial mistake is much greater there. I started with a worn model 10 from the 1970's.
Having said that, I made mistakes with that gun, like not checking some of the spec clearances, or at least paying attention to them. Lateral play - cylinder lockup is easy to check without a gauge, but cylinder gap is probably something that should be checked with a feeler gauge when you're first starting out. After you get some experience, you can sort of eyeball the gap to tell if it's too wide or narrow. The gap on that first gun was as wide as .016 in places...way too much really, though it didn't keep the gun from functioning (and shooting quite accurately, in fact.)
Checking the timing is easier on 6 shot K frames than 5 shot J frames (which seem to have less margin of error.) My preferred way of checking timing now is with el cheapo plastic snap caps/dummy rounds that show the indentation of the firing pin. In dozens of S&W vintage revolvers I've never had one with unacceptable timing.
I bought that gun about 7 or 8 years ago, and I did pay too much, for the time - $345. Was worth about 50 to 75 bucks less than that, but I don't worry about things like that...because I start out with the least expensive models.
I would say that the biggest problem most people run into when first buying nicer guns is not paying enough attention to originality. Serial numbers on grips, and (if old enough) barrels and cylinders aren't checked like they should be. Also, it's harder for beginners to tell original from a good refinish.