Also does your boat have an adjustable goose neck. The goose neck is the part of the boom that connects to the mast. Some of them can go up and down.
If it is adjustable you can get the luff tighter by leaving it loose and letting it ride up.
then after tying off the halyard their is often another line that lets you pull the boom down making the luff tighter.
There's a small loop of line that goes from the boom over a small knob/button/whatever on the lower part of the mast and prevents the boom from riding up. So, I could potentially do what you suggest by leaving that loop off until the sail is raised, but there's no downhaul or anything to bring it back down, except for the mainsheet.
Also check the shive (wheel) at the top of the mast.
If it is frozen or not working properly it is hard to get the sail to set right.
Yep, definitely frozen. I noticed that before, but decided to go sailing anyway
I was thinking about trying to get some lube in there and see if I could free them, but wasn't sure how it would affect the halyards. They also don't seem to be attached with normal fittings - it seems like they'll have to be pressed or drilled out if I go to replace them. Is that typical?
Lastly get some McLube Sailcote from West Marine and spray the sail slugs and track.
What does your main sail feel like:
1. old t-shirt
2. Really good oxford dress shirt
3. Really thick brown paper bag
4. Heavy stiff plastic.
The newer a sail is the more hard, stiff and crinkly it feels.
If it feels soft it is severely worn.
If it has no rips or tears the sail-maker may be able to refresh it for you for something you are willing to pay.
If not it will work just not optimally until it breaks.
Then google for used sails and see what you can find.
As a newbie, it's tough for me to say. Based on your descriptions, I'd say somewhere between 2 and 3.
I've started looking up sailmakers and will start calling around next week to see if someone is willing to take a look at it. Unfortunately, there aren't any near me, but the coast is only an hour away, so...