Bottom Paint Question

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My boat had bottom paint on it before. It is flaking off and am wondering if it is really necessary to reapply it again since i trailer my boat almost all of the time.I know that if you leave a boat in for an extended time the gel coat will bubble and crack. I am going to put it in a slip through the month of june next summer on lake erie. It is cheaper for me to rent the slip for the month then by the weekend. So my question is, is it something i should do if the boat is only going to be in the water for four weeks then back on the trailer for the most part, and possibly over the three holiday weekends for three days.