Wow, sounds like yours is similiar to mine. My other boat (soon to be sold I hope) has a winch on the boom near the mast that I use a lot. In high winds, I really like to flatten it out and the outhaul is one of the vehicles I use for that aside from the traveller and vang. Not having the ability to get some kind of purchase on the outhaul seems really strange to me. We'll see what the other 38 owners have to say.
Aside from that, the boat is amazing. I've been really surprised at how tender it is based on 3 days of sailing on SF Bay last week. I was going to the first reef at about 18 apparent with a 90% furler. That seemed really low, but I picked up a knot in the process so flat is fast on this boat! We also had it out in around 35 knots with only the main and she handled really nicely, but at the cost of not pointing worth a s^%t. That is to be expected though and it is nice figuring out the different configurations for conditions, especially prior to my wife being on board.
I had a real hard time accessing the pump for the hold out tank. It ends up they changed it based on the photos I saw plumping work on the other 38 (I forget whos it is at this time). In the photos, I see the manual pump is below the sink. On my boat, it is behind the head. I tried to cut an access hole inside the sliding vanity, but the glass was way to thick (surprising since it is not structural). I ended up removing the sink and could barely reach behind to get to it. I will reinstall it below the sink like they did in later years likely for the reasons I have noted. I'll likely put a piece of teak over the old hole with something to the affect of (if your hitting this, you need to aim lower!).
I absolutely love the boat and having a nice fridge (the norcold works great) and an inverter is REALLY nice. I would say, the only upgrades I would anticipate over the next few years aside from sails are a forced air heater and radar. The rest will be routine maintenance or replacement of things that break.
The boat is remarkably fast and will be a lot of fun to cruise and race...I'm very happy to say the least. I'll be happier when I sell my E32 though.
regards
shaun