With a couple of years to launch you have the time to take a few Americas Boating Club (AKA US Sail & Power Squadron) courses to freshen up and add to your skill set. In addition to the education piece you get to expand your network of folks with common interests. The courses are very well done and generally taught by experienced volunteers so the cost is reasonable when compared to for profit training.
If serious about the loop you also should be looking at the various route options and limitations re: air & water draft. The NE section(s) of the loop provide many options for some spectacular cruising that will take more than 1 season. Many do this as a multi season cruise by storing the boat over the winter and returning for another season of exploring. Others complete the loop and return to explore the areas / routes they bypassed the first time.
Best of luck with the search and adventures
BTW - Bought our Mainship at Eagle Point on Lewisville Lk
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Don
2008 MS 34 HT Trawler
"Bacchus"
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