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Adding insulationis only one piece of the puzzle. The object is to keep the attic space roughly the same temperature as the ambient outside air. This is accomplished via insulating the building envelope to keep your heat IN the building, AND proper ventilation of the attic space to move air around and through the attic. Adding insulation can help with the former, while making surte tha you have proper ventilation is also key. In many cases, the design of the roof or the environment the home is in isn't conducive to these static techniques and ice will form anyway. In those cases, we've had 100% success with properly installing ice melt systems along those sections of roof and gutter to allow water to work its way down through the gutters and downspouts and not build up behind an ice dam. See in the pic the area with the cables, and to the right the area without (which we've since added!) Good luck!
The killer mistake that people make is they let money become too big a deciding criteria, and then suffer through the whole project because of it. First, don't do that! Don't let the money become a bigger part of the process than the quality of service you want. Reputable contractors in any given area are buying from mostly the same vendors, so there aren't major differences in pricing. Interview the firms you are interested, find one that you feel a high level of trust for. If you "feel" one is going to be more expensive than another, examine that feeling and ask yourself if it isn't just because that firm might have a better handle on the entire scope of your project and their responsibilities within that scope than firms that might tend to gloss over things like that. Decide on the firm based on if you want to work with THAT firm or not.
That said, also make sure to write out a list of all the things you'd like to have when all is said and done, and then prioritize them, so you don't forget or bail on something important to you. And then- have fun!
I assume by "cave" you might been "cove" or some other trim or millwork. It isn't a hard thing to fill any scratches, resand, and touch up an area like that, and that's something your builder should have no problem doing for you. Good luck!
We have a sister company (Wine Cellar Technologies- www.winecellartech.com ) that handles all our cellar creation needs. Through WCT we've done commercial and residential design/installs etc. The racking we like using and looks best is generally made from Redwoood or Mahogany. If you have the budget for it, walnut or teak would be an awesome material to use as well. The exact design always depends on what the clients want to cellar, what they like, where they buy from etc. Of course we're biased, but having bought racking from all the largest racking companies over the years, the racks from WCT can't be beat for their quality, ease of installation, and beauty.
We actually have given up recommending our customers install gutter covers in our service area and regularly remove them. Instead, we offer a cleaning service that keeps the downspouts clear, and works totally every time. The gutter covers work, except when they don't. Heavy rains defeat the solid gutter covers (which is when you really want your gutters and downspouts to take in the water), and the screens allow enough smaller debris through that they still clog in our area and then are in our way for cleaning. Your location and tree cover will dictate whether or not such a cover makes sense for you. They wouldn't stay in business if they didn't work for some people, but in our area they seem to make more problems than solutions.
We've used Kohler generators for years and had great experiences both from the sales staff and the service staff. They have great options now for the transfer switches with options for locking out specific loads without having to go to the expense of a separate generator panel. The specific size/design/installation is best left to your professional electrician- Good luck!
After 30 days most likely areas that might have issues are any fixtures or appliances- mostly they have an issue right away or are good for many years! Also, check under your sinks to make sure that the use of the sinks and faucets hasn't allowed any of the fittings to come loose. We use brass fittings and traps, but many contractors have moved to plastic which can become loose with initial use. Another thing we find occasionally is that 3/4/5 way switches might not have been wired properly, which sometimes only becomes apparent when someone starts living in the home. If you have a home control system, that can be something that might need to be tweaked or adjusted for your use. Using everything, making sure that everything works, those things are key in the first 30 days- Good luck!