Fundraising Legalities

Maybe some of you could help.
I know, from a club I'm in that does raffles, that raffles are regulated, as it's a form of gambling. But there's all sorts of qualifiers to that that I've heard of... like, it's okay if it's under $1,000 and the whole thing is done within 8 days? And it's okay if... something to do with who it is who is doing the raffle itself.
I also learnt today that there's regulations on asking for money on the street, but it sounds like it's only if it's an actual charitable donation (so ... environment groups don't count as charitable, according to the example), and where it is you're asking for money...
I'm so confused.

I had been considering doing some sort of fundraising competition on here, but it seems like that wouldn't be allowed now.

Does anyone know if I ran a few events, and had some of the entry fee money going to helping my friend, if that would be legal? I'm pretty sure it would be.