Trip got pushed back a day... So here's a few thoughts.
Sidebar widgets are pretty simple. First you need to learn how to build containers which you can do either with a plugin that shows php code or as an actual block [more control, more work].
Once you have your empty widget you'll need to write a new query pulling either the latest reviews [with a join to get the product data] or random products.
Each product has all the needed details self contained so you can just format the output with images [easy since you use the uploader] and no needing to reconstruction anything like you would a vB post or setting.
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