Hi! if i may advise:
you yourself say you will use the money to "buy another bag I love more," which to me indicates that the reissue probably isn't the one for you and is just the best alternative for you right now, given your finances + current lifestyle.
i personally wouldn't do this thing where i buy a second alternative now just to resell it again in the near future to get another one i really like because it feels very messy and all over the place, at least to me. and there's no guarantee that the resale for whatever bag you buy now will be consistent, you know? so instead of being more afraid about the resale value, perhaps you could be less afraid of not using the bag and letting it sit in the closet. i assure you once you get the cc classic you'll find ways to use it because it's a beauty lol! and may i also suggest, just get the classic CC and then find another non-chanel alternative to use as an everyday lifestyle bag, until you climb the ladder enough to use the classic CC. At least, that's what i'll do.