I would like 99 of these, and 99 of those, and 99 tents to pitch at the hottie.

I rarely ever buy any actual healing items. Occasionally I'll pick up a few Tents or revive items if enemies/teasure chests have been stingy about dropping them, but by and large 100% of my money goes into upgrading my equipment. Unless my gear is at the maximum level available, I am not happy. This usually isn't a problem though, because most games assume item purchases in their money acquisition curves.

I never played past Suikoden 2, but my policy there was to just pick a core selection of teammates and focus on upgrading only the people I actually expected to be using. With the exception of one part in Suikoden 2 which requires you to have about 18 combat-ready characters, this policy worked out pretty well for me.

I find that works well in most games with large casts, actually. Instead of trying to use everyone, especially if party membership is mutually exclusive, just pick your favorites and let the rest sit on their duffs in the rear rank. It's more economical that way, and you'll probably be able to carry the dead weight with your maxed out guys when you're given a forced party structure.

Money was never an issue in Suikoden 1, though. Since you can save your game on the same floor as Gaspar, I'd just keep winning millions and millions of moneys off the dice game. Too bad they caught wise and set an upper limit to how much you can bet at one time in SK2.

Jam it back in, in the dark.