I have done a lot of buying and selling on ebay, and it is arrogant and retarded to list several similar items seconds or minutes apart from each other, in my opinion. However, almost without exception, when I have said this to a seller, I have been barraged with scorn and "don't tell me how to run my business I know more than you do" type of responses.
As a buyer who almost always snipes (the only way to play, if you don't - you only screw yourself - because everybody else DOES) I rarely place proxy bids on multiple items.
There are 2 reasons: first, I don't have a lot of spare money to waste, and second, I usually only want one specimen of whatever it is.
So, in a situation where a seller lists multiples of what I want, close together, I play mind games with myself and usually place a single bid on one of the later items.
It seems that the higher bidders shoot their wads on the earlier items, and there is a better chance later. Some of the time, anyway.
As a seller, I have usually listed the "better" examples first, but often get the best prices for the second "inferior" ones, presumably from buyers irritated and irrational from not getting the first one.
In case anybody (seller) out there cares, if you have multiples of similar items not listed as "Buy-It-Now" (the only serious way to list) then place them at least 12 hours apart and give buyers the opportunity to re-evaluate between each "round" and you may find that you get better and more consistent prices for your goods.
As to whether to list best-to-worst or worst-to-best, you might even consider being totally forthcoming and saying "I have 4 of these to list in the next week, and this is the best of the lot"
OMG, someone being honest and truthful - amazing!