Yes to both

It seems really weird and arbitrary. Sometimes they enforce 8. Sometimes they don't. I wouldn't count on it not being enforced. They do seem to definitely enforce the $1000 max in ebay gc per order.
I just tried my first $200 ebay gc order from Target. It worked like a charm (I ordered a single gift card, nothing else, no portal, received code in a little over an hour). Now, I have to decide if I do another $200 ebay, or maybe a few $100 ebay in a single order. I got a total of $1650 in target cards today, but I only put $600 on my account so far, and already had close to $90. I'm hoping to stay under the radar. I'm thinking I'll do a few $100s in an order tonight, tomorrow add a few more gc, order another $200, wait a day or so, add a few cards, etc. Kind of spread them out. Unless, of course, there's an ebay bucks deal.