I still don't get the buying part of the game, which is probably my biggest failure with it. Where can you buy something like a Tabula Rasa? I've only ever seen magic items at best when I've bothered looking at the purchase items of the NPCs.

I did however use some handy items from some on the latest character as bases for improving them because they had the right sockets already for what I wanted and were improvements on what I already had.

Most certainly, second and onwards characters always help, with stashed cast offs and/or saved currency. Even stashed gems are useful if you haven't leveled them up :)