Wow, lot of responses. The roller furler was a popular suggestion. I would have to qualify any response with insight into how you sail. The most relevant questions:
- Do you normally/frequently single-hand?
- When you don't single-hand, how capable is your foredeck crew?
- How experienced are you?
The answers to these questions have a big impact on what I think you should focus on. For me, the roller furler is no big deal. I never single-hand, I have a cracking crew, and I have strong experience. There are times when we get tired of taking down and putting up headsails, and in this region conditions can change frequently and radically. But, in the grand scheme of things it just isn't a high priority (not compared to some of the other items on the list).
I'll take the traveler off the list for now, since it doesn't really submit to the same criteria as the other items. The boom vang might be considered under the same criteria as the traveler, but I think it still falls under the criteria of safety and convenience.
I would just go ahead and move the tiller tamer to the top of the list since it is so cheap, simple, and greatly extends what you can do on the boat, whether single-handing or otherwise. Since it is so inexpensive, compared to the other items, and it is so frequently useful, I would put it straight to the top of the list.
This just leaves the boom vang, reefing system, halyards, and furler.
If you rarely single-hand, and have a good crew, then running the halyards aft would be a very low priority. The reefing system would be just above that. Both of these items are valuable in terms of safety and convenience, but both are optional with a good crew. Where the furler fits in to priorities has more to do with your experience and the fitness of your crew. If either of these is in doubt, consider the furler before the vang.
If you usually/frequently single-hand, then this puts the furler straight to the top of the list, followed by running the main halyard aft, followed by the reefing system.
The boom vang is almost in a class all its own. It doesn't really fit under considerations primarily dealing with performance tweaking, as does the traveler, but it is not as contributory to safety and convenience as the other items. You might not want to make it your highest priority, but I would definitely consider it before the traveler. Then again, if you never single-hand and you have a very strong crew, this item may float higher up the list as some of the other items become less critical.
I'll take some flack for this, but regardless of the type of sailing you do (unless you are primarily concerned with performance over safety and convenience), the traveler just isn't that important. Yes, it can contribute to safety, but not as much as most of the other items, and only if properly used. Otherwise it can make matters worse.
So, I'll try to simplify my suggestions.
First, get the tiller tamer and take it off the list. Cheap, easy to install, useful every time you sail.
Second, consider if performance is more important than safety and convenience. If so, put the traveler at or near the top of the list. Otherwise, put it at the bottom.
If you single-hand much, consider:
- Roller furler
- Main halyard aft
- Reefing system
- Boom vang
If you don't often single-hand, but your crew situation is not reliable:
- Roller furler
- Reefing system
- Boom vang
- Main halyard aft
If you rarely single-hand and always have a strong crew:
- Boom vang
- Roller furler
- Reefing system
- Main halyard aft
In this case, you might consider the reefing system before the roller furler, but probably not. I would, but I have fairly specific reasons for it.
I hope this helps.