Buy whatever trips your trigger and you'll start to figure out what you like. I kind of dived into the shallow end head first a bit and have learned a lot about what may or may not benefit from age and more about what I prefer with some different options. I don't think I started jarring anything until 2021 and have plenty of tins I've purchased set back which represent things I like. I still buy tobacco with age on it, now exclusively Virginias that are aged, and with advice gleaned on here, and so there is an aspect of "buying a cellar" which I enjoy, it is just much more focused. I've gotten what I think are some great buys from forum members on the tobacco FS sub-forum and have gotten some great buys from
@pipestud as well. An example - a few weeks ago while the clicking fury of the first few minutes of the auction were going on I saw a pack of 5 Dunhill Flake tins for about $30 a tin. I like Peterson Flake so I figured why not get what should be the same blend with 6 years of age on it. I've been airing a tin for a bit and will give some a go next week and we'll see if I can tell a difference. I found I like Capstan Blue (and Gold for that matter) and there was a package deal with some 2019 tins recently (still some to be found out there, btw) and and worth it to me to get some and it's packed away somewhere and would also make a nice Secret Santa gift as well. But it's all mostly an experiment. I have some old McClellands, some cost a bit more than others, and frankly mostly scratched that itch but found a few blends that I really like of that and not the over the top expensive ones and keep a lookout now and then. Mostly I try quite a bit of current things on spec to see what I like and if I really like something then I'll get some extra and put it back, most of that current sampling is aros and some lighter English blends. There are quite a few aro/non-aro Wilke blends in particular I like, I suppose because that is where I really started with getting sample packs, etc.
For me what is fun (may not sound like it) is trying something and finding I just don't care for it. I got a couple of the Country Squire Christmas blends in small quantities around the holidays --- one I really liked (and now put away until next Christmas season, one I finally tried just the other day and just didn't. I'll try some more of it sitting on the deck when spring comes and see if a different day/environment matters and if I don't like it then, it won't be saved, but I'm learning some things about some aros I just don't like when they burn, haha, and can taste a little acrid, to say the least. Just a flavor thing, but learning! Point is, I'm more intentional now and better for it, but only because I've experimented.
It's always IMO and YMMV, just like some beverages taste great and some just don't and some taste great in different contexts. I'll have a 7up every six months or so, but hand me a Sprite and you will get it back (unless I'm your guest!). I'm not a big alcohol consumer at all, but developed a taste for whisky (and now whiskey) and have a wee dram every once in awhile and I definitely know my preferences (got a pretty good education on a couple of vacations from some locals and bartenders who were really helpful) - if it is "peaty" I pass, haha, but my oldest daughter won't have anything that isn't. I have a very few bottles of what I really like and a few of those bottles I've had for a few years and they still taste great and haven't bought anything new since last year when I discovered some Irish I really liked and lucky for me the ones I like are pretty "common". So I guess I have a cellar, lol. Wine? Enjoy it if you like it, I just don't. Beer? Pale and simple and really cold, but not that often.
So I say experiment and do what you like, take in advice and read up on here and plenty to learn, I've learned a lot since 2020 and still learning!
Way too long a post, but something about the OP struck a chord, so, lol, IMO and YMMV and if you want to buy a bit of aged tobacco to see what you think then . . . . WTF!