S2 7.9 Bear Lake, UT
The policy I used when trying to decide on which airplane to buy seems suitable for the sailboat choice as well. Get what you really want, the bigger more capable craft. But be very conservative in the way you use it until your doubts fade and your rough condition experience increases. Be especially cautious about increasing the difficulty of reachIng a safe haven. Get experienced help onboard to develop your judgment and exercised skills when weather is somewhat challenging and do so with only sailors on board. Armchair help and advice just inspires overconfidence. Reduce your limits when short handed. You aren’t a professional scheduled service so be very loose on predicted arrival times so you don’t feel pressured to go when you should wait.
I don't know the comparison of flying and sailing holds up. There are very few boats or situations inherently dangerous in sailing as there is in aviation.