I would not feel comfortable giving my credit card number or PayPal account, so I would not join such event. Putting that aside, what about a prize for best game?
Cash Prize Tournaments?

How do you handle technical issues? Think, disconnect losses? People already get pretty upset when only a virtual rating or electronic trophy is on the line.

Online gaming isn't nearly serious enough for prize money tournaments. I don't care about the preponderance if easy online cheaters robbing me of a few rating points, but hard cash is another issue altogether. Way too much incentive to cheat and no ability to catch it.

Idea is fine, but as others have said there is no way to assure fair play.
Best suggestion from me reduce the number to close & trusted friends, people you are already familiar with & have a gentleman's bet.
We used to play $5 bets in golf, it wasn't about the money, it was about the look on the guys face when he handed you the 5 bucks.
Pride bet is another term.
Lot of fun in that. 10 guys = $50 pot. Build from there.
Be interested if you find 10 guys by the way.
No, I won't play, am more interested in the process.
Hello everyone! What is your opinion on online entry fee, and cash prize tournaments?
What time control would you be interested in joining?
How does this sound?
$15 entry fee with $360 in prizes based on 30 paid entries. 1St $180, 2nd $90 Best under 1900 and 1500 $45 each.
Or take the survey at surveymonkey: https://www.surveymonkey.com/r/63JTYQ3
Thanks!