I'm so sorry w/being late in replying, I honestly thought I already wrote/sent my reply!
For japanese blogs, I usually go through ameblog(アメブロ)which has lots of people talking about their shopping experience in Hemres (some in a funny way, some dead serious. Lots of people reporting their Hermes Patrol, which people here call their daily Hermes visit to find a free B/K). I wouldn't take all of them seriously, but it will at least let you see what everyone is interested in, and what's going around.
Yes, the resell market is crazy high, especially for the small size bags. I think its gotten worse because the Japanese reseller market is so popular worldwide, they can sell stuff even at that price range. I haven't really gone to omotesando much (just once or twice to get my scarf dip dyed), so I really can't say for sure of how the stock and variety is for there. As I've said before, Ginza is the flagship maison, so the number of stock will be the highest in Japan, but it also means you will have lots of people to compete with. If omotesando is easier for you to access, I would try to find an SA there you can click with, and start from there. I don't have any suggestions about what to buy, I'm sure there's lots of people who can comment on that better than me (I'm mainly a scarf fiend, so my shopping list will make no sense for most people lol). Hope this helps!
PS- please don't yuck your 35! As an almost 50 person, it's an absolutely wonderful age to be!!