My original cottage toolkit was woefully inadequate; left-over from my days as an apartment-dwelling student, it was little more than a tackle box crammed with an assortment of tools and equipment that I had "inherited" from previous roommates, or when absolutely necessary, picked-up piecemeal from corner and dollar stores.
While it was usually up to the tasks of picture hanging or furniture assembly, my toolkit was not something you would want to rely on when it came time to open the cottage for the season.
Neighbour Dan told me that he had a similar problem when he first bought his cottage. His solution was to head to the hardware store, grab one of everything that he was missing and slap down the credit card; $2500.00 later, he was all ready to go. I quickly decided that this wasn't the way to go for me. Not only did I want to acquire my equipment gradually, as the need materialized, but I also didn't want the initial outlay for the basics to hurt quite that much...after all, we'd just parted with a hefty cottage down payment and all sorts of acquisition related fees and taxes.
While I'm all for spending a little extra on quality tools to ensure quality results, the truth of the matter is that you will very likely only use a limited sub-set of your toolkit on regular basis. You'll find that you repeatedly use the same few socket sizes, the same couple of drill bits, the same screwdriver heads, and so on, while rarely, if ever, touching others. What you need to do is figure out how to avoid heading back to the hardware store every other day.
The solution? Buy a complete set of tools in a compact and portable case on the cheap, and should any of those fail through overuse or due to poor quality construction, simply replace them with some higher end gear. With any luck, they'll fit in the same slot as the tool that you're replacing, but even if it doesn't just throw it onto your tool belt for even quicker and more convenient access.
Here's my particular choice, and I have to say that I haven't had to replace a single piece of it yet: the Jobmate 415-Piece Tool Kit. (Remember that
only delivers within Canada, and that if you wait a couple of weeks, you can likely get this item on sale; mine was 60% off the regular price).