Simon's giftcards are interesting. Also, if in the USA it's possible you might be able to find them at your local mall...depending on where you are. If that is true, you walk up to the information booth at the mall and hand over cold cash, minimum $20 up to max $500, and walk out with the card for less than what the site charges. At my local mall it's $2.00 per card, no minimum or maximum number of cards. Also, my understanding is no maximum dollar amount to be handed over...so you could buy multiple $500 dollar cards.
However, I think Paypal's system is somewhat hip to them. The cards work for a little while and then Paypal starts requiring a different type of payment or a different card to be added to the account, whether Simon Cards or other brands of Visa card. I have been experimenting (read pushing the limits) with what I can do with Visa and/or MasterCard logo'd gift cards for some time just to see what works and doesn't, and I have noticed a recent change in the way Paypal handles them.
Sometimes when setting up a new account it does not like some gift cards, and sometimes..depending on the system's hiccups...it dislikes the Simon cards too. I've had best luck when clicking that I don't have a Paypal account and just want to buy something from someone...fill out the info with the address and everything (hint, dont' want 2 use yours, try Realtor*com for a US address if necessary) and just pay for the item I want to buy. Then after payment is made Paypal's system will remember the info and ask (practically beg) you to open a Paypal account. Go for it!
You can verify the account by letting Paypal do their little $1.95 charge and then sending your bank (read online giftcard billing account details) a number inserted somewhere within the billing details for the $1.95. So far the verify (or confirm or whatever they call it) has been sent within 30 minutes even though their system claims it takes a couple of days.
Another card I used to have fun with but doesn't work out so well anymore (still works somewhat, just not as good as it used to) is VanillaVisa or VanillaMastercard (*com). If you need to make an internet purchase you can register the zip code (but not the street address, which some systems require in order to verify the card details) at VanillaBillpay*com. Don't let the MasterCard logo on the site fool you, it works to register the Visa cards too.
Lately the VanillaVisa and VanillaMasterCards have been showing up in grocery stores, as well as Office Depot.
Speaking of Office Depot, stay away from the American Express giftcard. Bought one for $200, went to use it to make an online purchase, and it was declined. Called their people and was told that some merchants will take the Amex credit card but not the Amex giftcard. Since normally the sellers of these giftcards do not want to make refunds I thought I was stuck. Luckily when I returned it where I bought it I explained to the cashier that I bought the card to make a specific purchase at a website that was rejecting it. Told her I was buying a script from a programmer for my website and the money on the card that was being rejected was my only way to pay. So the cashier went beyond store policy...the cash register literally would not ring up the exchange...and gave me the money back in order for me to give it right back to her to purchase a different gift card...VanillaVisa...that worked flawlessly for my purchase.
So it's not true what they say..."American Express...everywhere you want to be."...like they say in their stupid commercials.
Just thought you'd like to know...
HTH