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I cannot speak to all versions of the various Kindles, Fires and Kindle apps (not to mention Audible apps), but I think it is the case that those which have been updated in the last 6 months sync to 'most recent' position, and not 'furthest read'. This should work for both books and personal documents. On such devices/apps, there is usually also a way to go to 'furthest page read' (but not for 'personal documents', at least with the reading apps I checked just now).
This makes it trivial to reset the reading position: just go to the desired position, and sync (when online). Any of the devices or apps that understand 'most recent' will pick that up and offer the option to jump to a 'most recent' location, if one exists.
Older devices, like PW1, still want to go to 'furthest page read'.
In my opinion 'most recent' is usually the more appropriate choice. 'Furthest read' as this thread evidences, is fraught with inconvenience should you accidentally jump and sync to a location, as it is a 'monotonically increasing' function and must be reset by going to MYX. 'Most recent' can get you 'lost' also, but at least you can re-establish it on any device. It also works well for reference books where you may jump around more, rather than reading linearly.
That said, I find sync doesn't always handle every scenario correctly (even in the sunny day cases where devices have constant internet connections), particularly with switching between audiobook and ebook (on a single Fire device even). And sometimes the choice offered makes no sense, for example I may listen to an audiobook while offline, and when coming back online it offers to go to a 'most recent' (but past and previous) location on some other device, even though I just spent a couple of hours going further, and the timestamp for the achieved location is clearly both more recent and further than location reported for the other device. So I don't think they have a solid 'sync test plan' in place as they update things.
It's a pretty big and growing matrix of combinations that need testing, and much larger than any other vendor has to deal with, but it is an important feature and the effort should be justified.
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