I would watch Ebay for a used autopilot. While a wheel makes it more expensive, there are deals to be had. I bought my tillerpilot for less than 80 bucks. I can tell you that while my main purpose for the tillerpilot was to enable single handing, it changed my sailing life. I sail to relax. I'd be just as happy to be a passenger as the skipper. AutoPilot has enabled me to do that. Just cruise along and let the boat do its thing. So while it really helps single handing, I'd have bought it, just for the major improvement in the quality of my sailing enjoyment.
I'd also highly recommend some sort of lazy jack system. While technically my system does not raise up and down, it does catch the sail and keep it from falling off the boom. When the sail is up, it holds the boom level, which puts slack in the catch lines. When the sail drops, the boom drops and pull the lines tight, which catches the sail. Simple system and cheap - probably 25 bucks for everything. I don't use a downhaul. I can pull down enough on the leach to get the sail down. Because the boom drops, I can reach it from the cockpit.
The area where I sail has a fairly narrow channel back to the dock. Since I have to motor, with the autopilot, that gives me time to remove both sails and the boom and get everything put away inside the cabin. By the time I hit the launch ramp, the only thing left is to drop the mast, once its on the trailer.