Adding in my $0.02
I think the most important thing you can do, when collecting and starting out on a journey, is thinking about what your goal is, and then thinking about how easy it will be to transition to a new goal if you decide to.
I was out of the hobby for like 20 years. When I got back in a few years ago, I really was kind of aimless. I eventually settled on the 1953 Topps set. I set out on completing a set, all PSA graded, at 5 or higher. I got most of the way through, and then decided I didn't want to keep going, so I had to pivot. When I went into that set, I told myself if I ever lost the desire for it, I wouldn't keep going just to "get to 100%" because we aren't talking about trivial amounts of money.
On the macro level, you should figure out what your goal is. You listed a dream budget of $2500, and you said you liked a few players. I'm not saying this next part as a judgment of any kind, so don't take it that way. But is your goal just to buy a few T206 cards of big names? Is your goal to collect an entire set? Are you interested in a certain team? A certain type of card?
You can buy a WaJo or Cy Young or Ty Cobb for $2500. Once you buy that card, is that the end of the journey? Do you want to eventually collect the 520 card set? Do you only want the Hall of Famers? Are you looking to buy a card now and sell it for more later? All of those questions will impact the path you go down.
Are graded cards better? Well, that depends who you ask. I have close to 150 different T206 front/back combos, and all of them are now raw. I cracked some of them out of slabs. I did this because I want my entire collection in a binder (2 binders, actually). That was a conscious choice I made, with the understanding that if I crack out a PSA 2 and then I want to eventually sell it raw, I will get slightly less for it when selling it.
The big name cards in the set retain their value, and the value will increase. If you bought that WaJo that Luke posted above for $1900, there is a good chance you can sell it for $2200+ in 6-12 months, maybe more. The big names hold their value, and the value will keep increasing.
Before you buy any cards, you should think about what your goal is, and then think about what you might want to pivot to down the road. I started out thinking I would just collect a 520 set, with varying backs of the cards. I then realized I wasn't really interested in doing that, and instead I only wanted to collect portraits, and I wanted to collect all the front/back combos for every player that has a portrait (except Wagner, Plank and the Magee error, for obvious reasons). When I came to this realization, I determined buying graded cards wasn't really going to be an option because of cost, and that I had to make concessions on quality.
I can't speak for everyone, but most people usually deviate from their Plan A and sometimes even their Plan B and C. Good luck figuring out the path you want to take, this board is definitely the right place to ask questions and learn lots of great information.
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My T206 research thread
My T205 Census thread
Want list: M101-2, T205s (American Beauties)
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