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Here is how I used to do it when I sold a bunch of stuff on ebay.
Do as you plan with pre-packing everything. For small stuff, as people have said, padded envelopes are the best and cheapest way to go. If you go somewhere like Costco of Office Max you can buy large quantities of them for a decent price.
Take your pic(s) of the item and give the item a number. Write that number on the package and package the item up. Create a simple spreadsheet with four columns. the first has the item number, the second as the transaction number that ebay will assign the item when you put it up on the system. The third has the minimum price and forth has the price it sold for. You can make a fifth if you want for notes.
This way when the auction ends you can look at the transaction number, see what item number that is for you, grab that package and put it in the to ship box. Then mark it as done and you are good to go.
As for bulk listings. Use Ebay's free program called Turbo Lister. It will let you enter all the info into an easy fill in form and then you can upload it all at once. It will save you a lot of time. Also, depending on your setup if you buy the right blank labels you can print shipping labels right through the ebay interface now.
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