Try breaking the issues down.
We can't advise you on the business investment thing - or at least, I can't.
But most of us are in a pretty good position to have a view on skating and what it means for old gits like us.
So, first thing: are you interested mainly in talking about skating, or in doing it?
If you're interested in doing it, what are your main obstacles?
If it's the lack of a board, that's easily sorted. EIther you buy one, or - as you've seen - you can have a spare one, free. And don't be put off by there being other more 'deserving' people in the world: that's a slippery slope that just leads to a 'how can I ever justify enjoying myself when there are starving people in the world' mentality. There always will be people worse off than yourself: that's life.
If it's lack of confidence that's stopping you skating, what is behind it?
Is it physical confidence? Do you worry that you'll be crap, and that you'll fall off and hurt yourself? If so, hook up with some other old skaters - we all have those issues from time to time, and we enjoy the company in being old and lame together.
Is it social confidence? Do you worry about what people will think of you if they see someone of your age on a board? If so, see the answer above.
Or is it some other issue of confidence? Be specific about it, and then, if you want to skate enough, chances are that there will be a specific way around it.
Does that make sense?
What's your other forum, by the way? The one where all the people argue and show off about their gear?