The transition to a cat is not that big a deal if you’re comfortable operating a twin engine anything. As far as sailing, most things are the same except backwind the jib slightly thru tacks. Be real careful and watch your sail plan. Over sheeting is common to mono sailors.
Was at Bobby’s and Riteway’s 2 weeks ago in Road Town. Bobby’s was looking sparse while Riteway was pretty much like a local rural US IGA. Like you we’ve always used Bobby’s before but have used Rightway for the last 2 times. For beverages check Caribbean Cellars and Tico. Sometimes the cost difference will really get your attention.