It all depends on how you define ambition. I wouldn't really want a lot of things, certainly not a big house, because they are a nightmare to run on your own and a staff can be a nightmare to handle. However, I would want to be sole owner of the house I live in, with the deeds tucked away in a safe-deposit box somewhere. The one thing I would want is a boat, a sailing yacht (because I hate motorboats with the same vigour that some here hate Pacers). I'd also want the best camera money can buy. As for cars, there's nothing on the modern market worth buying. I'd much rather have a private aircraft, especially if I could do my own flying, although I'd probably fail the medical and have to employ someone else (but would still make sure I had a forward view no matter what).
I like the idea of running a TOC, because I want to do it properly. Absolutely no experience, of course, but I have a good sense of the proper way to do things on a railway. However, a good general manager would be absolutely necessary (partly to stop me spending huge sums of money on headboards and sprung seats). I'd still insist on sponsoring the GCR's bridge, though. It's probably the most worthwhile preservation project going at the moment, and one of the hardest to do.
Where a lot of it would go might well be travel. I've been meaning to visit the Falkland Islands for years - South Georgia as well if possible. Getting there aboard my own boat would be ideal. There are all sorts of other places, such as the Okavango Delta, Patagonia various places in Canada that take weeks to get to. Possibly northern Siberia one day as well.
Strange ambitions, but it's far easier when you can afford it.
