Well, I am not Jerry, but I have run at least as many or more raffles here than he has

I can say that because Every raffle but two that I can think of was run by me and Jerry or me and Jerry in the last eight years.
To run a raffle properly, you advertise it, ask for donations, we usually got around 10 prizes + and then you either literally or figuratively set aside numbers (I have used 'tickets' but then there is cost involved) and most recently used electronic tickets.
Some one sends me money via post office or Paypal - be advised that I lost a Paypal account, and ALL bank accounts tied to it by running the raffle, evidently it is against their rules.
So, you use paypal, you do it at your own risk. I then put out my PO Box and folks send me cash, checks or money orders.
I keep a spreadsheet of every 'ticket' and amount (1 ticket is $10, 5 tickets is $40 or the like) and that ticket also has to have the persons name.
you run the raffle for a month, longer and folks get bored, sooner and you can't collect enough money.
I have had folks send me the item and then I mailed it, bad idea, thats double postage.
Since I already give enough time to the forums, any expenses are deducted, paypal fees, postage, etc. I am very practical when I do this, but of course the object is to raise money, but also have fun for the folks.
If
am running it, i don't generally buy tickets.
Once the month is up, then I literally print out and cut up the ticket numbers (which has the persons name typed next to it) and put them in a box. I draw a number at a time. I have each prize numbered, then as I draw, that person won that prize. I try to make each 'prize' worth it, i.e. a $25 item like a repro holster, I would add another prize, like an original loading tool.
Once you have everything drawn, you notify the winners and paste results here on the forum.
Then you have to ensure the winners are hooked up with the prize givers.
So, the work is; getting prizes, pushing the raffle several times a week, drawing names, notifying and you're done.
Each raffle probably takes up 30-40 hrs of my time, at least...