Windsome 23,
I just checked out the Worst Marine web site, and they are selling the Autohelm 1000 St+ for about $480. That means that you could probably get it at another boat store for maybe $20 less. When I bought mine, they were selling for around $450 I think, and that was about two or three years ago. Most of the time, I sail off the dock, or off my mooring. Either way, my boat is always headed into the wind which makes it easy to raise the sail. If I'm at anchor, I'll raise the sail first, then pull the anchor up and walk back to the tiller and sail off. Sometimes when the wind is light, and I'm afloat, I'll raise the sail with the wind behind it. I know,-- it's really lazy and unsailorly of me, but occasionally I can do it and get away with it. I don't have anyone standing there saying, "Hey there, you can't do that!" Who cares, right? Anyway, I don't know what your boat does when you try to raise the sail or get it down, but mine will sometimes go in circles. It's a keel centerboard sloop, and I guess that it's just the nature of the beast. Keel boats have more gripe and are prone to point into the wind, but not these boats. So if the wind isn't too strong, let it go around. Hold on to her boom so she doesn't swing around too hard when the wind gets on the other side of the sail. I always raise my centerboard before I try to anchor under sail just in case she tries to go around in a circle. Getting your anchor line caught in your centerboard is no fun experience. You should be able to get an autopilot for way under $500 I think. You can also save a few bucks by building your own mounting pedestal like I did.