[Topnotchsy]

If you are looking at getting the items signed at shows, I would recommend staying away from team signed pieces. The cost of accumulating the signatures yourself will far, far exceed the resale value, and when you do it one at a time, there is a high likelihood that the signatures will not be particularly neat (as opposed to when a company gets all the players to sign the ball at a single event, using the same pens etc.)

If you are looking for a hobby/collecting experience, working on getting those balls signed is a great experience, and since you are chasing many players, you can find them at shows frequently, though again, partial team signed balls are not worth much, and certainly far less than you would have paid.

On the other hand, if you are buying the items pre-signed, I do think team-signed balls are a great way to go. Many people collect WS team-signed balls, and I think they tend to hold their value pretty nicely. Often the World Series MVP may not be someone so significant, and while interesting, they aren't always particularly memorable. For example, the 2018 Red Sox MVP was Steve Pearce.

Your focus on a HOF from the winning team is interesting, but is much less homogenous. How do you decide who to get? Also, during their careers it is not always easy to determine who will be a HOFer. You can always change it up, but for example for the Yankees run in the late 90's, Clemens would have been the most obvious for 2000 and he's not in. Bernie Williams and Andy Pettitte might have seemed like an options and they aren't in. Jeter and Mariano were very young then, so you might have gambled on them making it, or you might have stayed away thinking it was too soon.

Either way all are interesting and fun projects, but depending on how you approach this and what you want to get out of it might help you decide.

Just my $.02.