Re: It's a good time to buy from Japanese retailers
That might all be true, but if you want one anyway, USD buying power against JPY is at it's best right now.
I've only dealt with Fender Japan products tbh, tonewise it seems to vary from model to model rather than guitar to guitar. Fender Japan uses basswood for the most part, which tends to be pretty stable tone-wise; acoustically solid. The only MIJ's I dont care for tone-wise happened to have alder bodies.
Regarding damage in shipping, I've gone mostly through Ikebe and Ishibashi, but also others, and they have all packaged the guitars really well. Guitar in a gig bad, or beside a gig bag, in a box, wrapped in padding in yet another box, so altogether there's three to four inches of distance between the guitar and the outside of the packaging. Ebay sellers and US based retailers have tended to be a lot more skimpy with the packaging, often with no secondary box. The boxes I've received from EMS/USPS also tend to be free of dents, like they were handled well. Again, for whatever reason, domestically moved boxes always seem to be worse shape.
I can't comment on how the prices have changed over time since I wasn't shopping for them ten years ago. I really don't think they're that well know to the general public, though, just based on what I've seen in discussion forums. I think most people find what they want domestically and look no further. Compared the MIM and MIA, they aren't a great value, since you pay more for shipping (or whatever goes into that) that you'll never get back if/when you resell later. If they were 15% cheaper across the board, and had free shipping, they would be preferable to MIMs (and I think those price points would be obtainable if they were officially offered in North America). But if what they happen to be selling is worth the additional $150~ to you, as it is to me, then it's not a problem.
The ebay resale on the unique Fender Japan models has been pretty strong. If they are mint (by mint I mean "ebay mint"), they tend to go for more than what they had cost new if several years have elapsed since they were last offered new. I've seen this with limited edition Epiphones as well, like the Noel Gallagher Union Jack was $800 new(?), and go for $1500 - $2500 now. How well it stacks up against a traditional investment vehicle, I don't know, but it's not an unsafe purchase so long as you keep them free of wear and cosmetic damage.