It mightn’t be as easy as you think, RandomLetters. Firstly, catalogue prices don’t bear much resemblance to actual market value.
Secondly, the reason some cards etc are so valuable is because there are so few of them. You turn up with a bunch of stuff you may depress the market.
Thirdly, you will also have real problems convincing people that your stuff is genuine: due to being whisked forward in time fifty years, your cards and comics are going to be and look brand new, when if they are genuine they should be 50 years old. My guess is that many are going to think your stuff is fake.
Chronos I don’t think that gambling would be too much bother. You’ve got 6 months, and many forms of gambling are entirely anonymous. If you just make a few bets at one track (most random just for show, but say one big trifecta based on historic newspaper records) then act completely gobsmacked when you win, then move interstate and do it all again I don’t think you’ll arouse too many suspicions. As long as you don’t make your wins so huge that you get publicity, and as long as you always dress and act like just a regular guy who’s hit it big this one time, and don’t get flashy or appear rich you’d be OK.
Also, Chronos, I think the lawyer idea in your suggested form has problems. The biggest basic problem is that 50 years is a hellava long time for an estate with no known or contactable beneficiary to just hang around. Many lawyers would be very very suspicious as to what the hell the deal was when you walked into their office off the street and suggested such a thing. The type of lawyer who is not going to ask a lot of very hard to answer questions is not the type of lawyer you are going to want to trust to act appropriately for 50 years with no one to keep an eye on him. Heck, he or she’s probably going to retire and/or die in that time. What happens at that point? What is the structure you are going to set up? Any structure you set up has to have a beneficiary at the bottom? Who’s that?
What happens if the tax authorities hear about the situation (and they may well do, someone may well notice sooner or later that there is this massive property owner who no one has ever seen). They are going to ask to audit the client. Who is that? Why hasn’t the client ever paid any tax?
Nah, such an irregular based-on-trust arrangement is a bit dodgy if you ask me.
Here’s my modified suggestion. You start with your initial stake and build it up through whatever chosen means (gambling, stock investment etc) to a pretty impressive level.
Get a lawyer to draw up what would be a moderately complex but nonetheless workable trust deed setting up a trust. The deed will name as beneficiaries your own then-existing family. Tell the lawyer you are a family friend who wants to repay your family for a past good deed anonymously. Write guidance into the trust deed as to suitable investments. To avoid suspicion, it would probably be best if this guidance was fairly general (ie not “buy this company stock on such and such a date” but rather “invest in this type of company” and “invest in land in these general areas”). Tie the lawyers/investment advisors fees to outcomes.
Ensure that your family knows about the trust before your six months is up. You have now ensured that you have a group of people with a direct financial interest in the money to ensure that the lawyer/investment advisor don’t go astray, and to provide instructions if required, and to satisfy the tax authorities etc as to what is going on.
Allow your family only a certain income from the trust, not access to the whole income and certainly not to the capital.
Then, finally, shape the deed so that the whole trust fund vests in you, in 2004. The way to do this would be to ensure that the deed looks as if it was “drawn blind” but actually aims at you ie have it say for example “the whole fund shall vest in the first born grandson of [name your grandfather here]” or "the first member of the family to complete a Master’s degree in [insert your qualification here].
Of course, you start getting into severe time travel paradoxes here: if you go back and set this up then will that change the course of your family such that your planning will go wrong? Will your father (now a rich man) marry someone he otherwise wouldn’t so you are never born?