Your boots do sound a bit floppy with probably not that much shock absorption / protection, but it's really up to you – what you're comfortable with or want to put up with. A rigid 3 / 4 season boot may be a bit too stiff for your taste, I would maybe try a 3 season, especially as you'd like fabric - they're not too rigid and are pretty light, certainly ok for long summer walks and easy scrambling.
I wouldn't be too anti-leather though – newer ones are more comfortable than they used to be and require less breaking in, I use Scarpa SLs (3 / 4 season leather), these have just been updated with a bit more give and being lighter, but there might be some of the older ones still about which could be had for a bargain. Meindl also make good boots.
As for waterproofs I've always made do with cheapish trousers, after all your legs don't sweat as much as your top half, but I use a Goretex shell jacket. I have a couple of friends who use Regattas and are quite pleased with them. I suppose it all depends on how much you want to pay against performance / comfort and how much you're going to use them. Maybe try Berghaus Paclite though, if you want to pay that much….?
I'm sure the rucksack will be ok for summer gear, maybe a bit small for winter kit etc….?
I'm a big fan of Berghaus rucksacs – well made, good fit, not too expensive.
I wouldn't be too worried about the north ridge of Tryfan – no need for scrambling at all (well, almost) if you don't want it, Bristly Ridge onto Glyder Fach is trickier, but always avoidable