1) If you own four or more OSs: work _with_ a buyer before conversion. When you convert to a full sim from four OSs, you can rename and reposition it without charge. So, working with a buyer, it is exactly like buying a new sim from LL (for an existing sim, renaming costs $150, and repositioning costs $100.) What this means is that you can get more from four openspaces than from a single, existing full sim on resell.
You can submit everything as one ticket transaction. Just have you, and the purchaser, put in the details of the transfer/conversion in a single ticket: openspaces to convert/transfer, new name, new position, and price.
Tier: the tier date of the new sim upon transfer is an average of the tier dates of the four openspaces. Remember, when you buy new from LL, you get a free month's tier. Worst case scenario, the maximum value of four OSs transfered in the above way is $1000(setup cost) - $300 (month's tier) - $100 (transfer fee) or $600. The value in the best case scenario (full month's tier left) is $900. Now, there is no way one is going to recover all of the value, so I'd say price it at least $100 less than its full value or more, depending on how fast you want to sell/availability of buyers.
If you own less than two OSs: It is best to work with another OSs buyer to sell a total of four OSs. Otherwise, you can barely even _give away_ an individual OSs. There are two options for this, depending on whether or not LL allows two OSs owners to transfer a total of four openspaces to a third buyer in a single transaction for a single $100 fee. I put in a ticket asking on this and didn't get an immediate response (it is listed as "work in progress"

2) All as one transaction. For example, Party A has three OSs, and Party B has one. Both transfer/convert the total of four at the same time to Party B as one transaction for a single $100 fee. The economic figures are the same as 1), except that the proceeds are split proportionately among the two sellers.
3) Multiple transactions. Find someone to "fill your hole" to complete a set of four; three sellers results in more fees. Seller A first transfers his/her OSs to Seller B for a $100 fee, and then Seller B transfers them to Buyer C for an additional $100. The maximum value in this case is $800, and the minimum $500. Proceeds are split proportionately (if the proceeds are $500, for example, Seller A with 1 OSs would get $125 and Seller B would get $375.)