[JavaNut]

Not commenting on any legal issues.

But why not find a site where you can create private play money tables.

Then let a play money buy-in of say $1,000 represent say $50 in real money. After each evening note down how much play money each has left and convert that into real money.
And keep a tab on who owes who how much.

Making your own reliable poker client to be used over the internet can be done, but it will be quite a task to do so.