If it were me, I would be buying the boat with zero options (except those that MUST be done at the factory, like keel or rig) Because I can't see how anyone can justify charging $700 for a VHF, or $900 for a CD player, or $2000 for a 15" TV, or $2200 for helm sheeting, or I could go on and on and on. I started a thread on it, but I got the impression there that most people would rather roll up a wheelbarrow full of money than do a little work on their own.
Yes, this is what I did, I bought brand new with minimal options to keep the price down, in hindsight I should have rolled up a wheelbarrow full of money, time is money.
There are a few options that can and should be done by the factory for economies of scale since they can buy in hundred lots. Then there are options that are better done by your dealer so that you have someone close by to help when the need arises. Then there are those things you can do yourself but you better be handy, have the right tools for the job, and have the time to do it.
I had to do a lot myself and learn in the process. Sure I learned alot, and I know how every little thing was installed because I did it so if something fails I can trouble shoot it pretty fast.
That said it is still a major PITA to be a DIY kind of guy and the cost of doing something after the fact can be high. For example, I scrapped the rollerfurler option to save some $$, but within the first year I realized what a dumb decision it was. It took me a few more years to get a furler and install it myself and then have the hank-ons converted to #6 luff, after all was said and done it would have been less expensive and less frustrating to have taken the roller furler option at the outset. Ditto for several other options but I had to go to the school of hard knocks and learn the hard way. Yes I learned how to do a few things for myself but I also learned some lessons in frustration.
Like someone else said it is paramount that you have the confidence in your dealer to do the work properly otherwise it is best you do it yourself and endure the frustration, at least you know it is done to your satisfaction. Still if I thought my dealer could do a good job, and he has done some work for me in the past I would get him to do it. If the dealership changes management and you are not familiar with the new folks, you are taking a risk, back to DIY. My biggest complaint is that many dealers do not provide the level of aftermarket options/service that some buyers would like, and I would be one of those buyers with a wheelbarrow. It is just easier and less frustrating to have an experienced person do the work for you than have to learn yourself, at least that is my experience and I still engage in DIY projects just because I cannot always afford to pay someone else. Life sucks!