jhitesma,
Thank you so much for your quick and frank reply. I think you've convinced me to hold off for the moment.
The biggest reason I wanted to setup my Nook Classic with the Aldiko/Stanza/Trook-style catalog was that (a) it would be nice to be able to access my books via 3G and not be limited to the Nook Color Wi-Fi, and (b) the Nook Classic's longer battery life makes it the "go to" reader in the house for planning long trips.
Since I've since read that Trook only works over Wi-Fi (unless you do clever things to your SIM card) and you've informed me that mindfulness to detail (not a strong point for me) is required to prevent battery drain on a rooted Nook Classic, then that really changes the layout of the land a bit.
After all, it's not the end of the world to have to remember to sideload my Nook prior to a trip; I'm just the leading expert on spending hours (rooting) to save minutes (sideloading).
Thank you so much for all your help - you've really clarified a lot about Nook Classic rooting, and I feel a lot more informed now. Thank you!