Best Strategy After a Long Break, High Level?

The answer is yes. @evethemighty did it. See her study log here. If I recall correctly she just powered through her items until the job got done.

Perhaps some kind of reorder script will help you. Reorder Ultimate 2 posted by @cineebon will let you prioritize items by level. Then you will have to settle the lowest level before you move to the next one. This is kind of what you are looking for.

You may use Item Inspector to plan such a reset. This script will let you sort and display your leech items ordered by level. This will let you know which items are causing you most trouble and what level they are. Then you will know which level is worth resetting to and which don’t cause you enough trouble to be worth a reset. Disclosure: I am the author of Item Inspector.