Looks like it's been taken care of quite nicely. Same configuration as mine, and mine is also my first sailboat. As for what to look for, the usual suspects apply, and that's basically to say check the obvious places for leaks, like the chainplates, stanchions, deck hardware and around the front hatch. Assuming that's all good, then you should be fine. With new stuff already in place, upgraded winches and such, you're off to a good start.
I love my boat, even though it's not nearly as clean as your own. Mine was also very low budget to get into, which reflects it. I love the way it sails, it points upwind quite nicely, and is a joy to be on.
Only complaints I have for mine, are the relatively deep draft compared to other similar sized boats, but depending on the area might not be an issue at all. The other thing, the main reason that I'm ready to upgrade after three years, is the head room. I'm 6' tall and if you haven't set foot on it yet, you'll realize that sub-5' headroom for some people will get stuffy after a while. Obviously that also depends on the people, and the usage. I have no problem spending a few days at a time, and could do more if I really wanted to - in good weather. But if you're stuck inside at anchor on a rainy day, it's going to get stuffy in a hurry for most people. It's the single biggest wish I had, was more headroom. And that's very evident when using the head.
The V-berth could use a little more clearance above your head also, depending on who's spending time there. Smaller kids and people won't have as big a complaint, but anyone else is relegated to sliding in and out, and there's barely room to roll over if you've got wide shoulders. One of my potential plans this year (if I get around to it before selling the boat after this season), is to lower the V-berth. Even a few inches will feel like a giant upgrade in space up there. But as I sleep in the quarter or on the folded down table myself, it hasn't been a priority. For the anchoring duties for me, my primary is kept under the v-berth floor and fed out the hatch. That's also easier for me as I've replaced the head with a porta-potty which has eliminated the holding tank. I also don't use the water tank, even though it's still in place.
It really is a joy to sail though, and you've got enough upgrades to make it a great boat to learn on (I still have the old school winches and a hank-on headsail). If you're looking for a day sailer/cruiser, or something for a weekend, it'll be plenty good, and I've gotten a few "hey, what kind is that?!" comments in the short time I've owned her. She's got a sleek look to her, even for the age, and I've surprised a couple other boats in friendly races, even not counting the handicap. And that was with worn out sails - Upgraded sails like yours will be even better.
I'm sure your outboard will be more than plenty, though I'm not sure by the pictures if yours is mounted in the well, or off the transom. If it's in the well, be warned that you have pretty much zero control in reverse at slow speed, as the rudder is in front of the prop. So until you get some good movement of water, you'll have nothing. You pretty much need to get the boat moving, kick it in neutral so you aren't washing the rudder, and... well it's not easy until you're moving. If you have a bracket off the stern though, that eliminates that issue by virtue of having the ability to turn it as well.
Hopefully the trial goes well, but I think you're going to enjoy how she feels in the water. If you haven't read it yet, Todd Lipps has a good blog on the Ex26 that he owned (recently sold). Here's a great starting point of it. His blog was also what ultimately gave me the confidence to go ahead when I was looking at mine.