As far as buying replacements and upgrades goes, it comes with the territory on these boats. Mine's 10 years older than yours, and I created a list of things I wanted to repair, replace or upgrade when I bought it. That list has seemed to continue to grow... the more things I fix or upgrade, the more I find that needs to be! A lot of them are convenience items, though... all part of owning a boat.
1) I wouldn't worry about the SS gudgeons, if you can secure them more firmly, they should work just fine. If you bought SS pins, they won't wear like the AL ones.
2) If you sail with older rigging, you may be on borrowed time. However, if your boat is a fresh water boat, sailed lightly, or you continue to sail it lightly, it may be alright... the issue is that you just don't know, and dismasting is a scary thing. I know it's not recommended, and I'm sure srm would scold me for it, but I've been rotating through rigging replacement on my boat. It's just easier on the wallet, and the old rigging shows no sign of wear and has held up pretty well for me. If you're not going to use the trapeze just yet, don't worry about replacing them. musicman is right, the boat is much easier to handle from the wire, once you get a feel for it. But with wings, you'll already have the advantage of some extra leverage.
3) The low profile double block system is nice in that it's easy to set up and there's less friction in the system, but plenty of people still sail with the old system. The boom bales are intentionally angled, I believe.. or at least mine are that way... but I would save new mainsheet blocks for later on, and focus on tightening up the steering system for now.
Where in NY are you? I sail out of Buffalo, NY all the time