I'm glad to see that you are seriously attempting this run.
I highly recommend you record your progress in an .fcm even though it isn't an optimized run at all. by replaying you can get more ideas and possibly catch things you would have otherwised missed. You should definately make a test run of a game before you attempt an optimized on, especially in an RPG as complicated as this. but at least make a movie and select record from "now" so that you can post it, so that I and others might be able to give comments.
one thing you want to look into is whether button presses affect the random outcome. (Read my DW4 posts for more info). This can give you significantly more options, and reduce the amount of wait time when trying to get random events.
The crest glitch thing looks very interesting but I have no idea how that might happen, it might be a result of bumping the console and getting glitched results (which in unfortunately un-reproducable on an emulator)
Also, look into what random enemy drops. You might be able to get some essential items, or some things to sell. I know bullwongs leave wizards rings which should be useful
this sight should be very helpful:
http://www.woodus.com/den/games/dw2nes/
also, do you think that the lottery would be helpful?