Dave, your family sure is talented ;^)! The custom Tron paintings are truly fantastic pieces and are no doubt the center pieces of your collection. I can't imagine how good it must feel to be given such a gift with all of the family history behind it. I know one of my favorite items in my collection is a $2 Batman figure that my fiancee bought for me and put on my 28th birthday cake. It's funny how little things (or in your case, awesome art ;^) can become such prized possessions.
It was not my idea to pad my collection by creating unique items. Far from it. My preference was to collect only legitimate items.
I think that's where most people start in the 'collecting world' in general. People usually start collecting because of sentimental reasons and look for items with a certain degree of familiarity. Usually this would mean production items that they remember from "way back." After a while though, most collectors branch out in their collecting and take a few tangents every now and then. Personally, collecting bootlegs is one area of toy collecting that I thoroughly enjoy. Sadly, there doesn't seem to be much in the way of bootleg Tron stuff out there so thankfully I collect other lines ;^).