Neverknow, good to hear that we didn’t inadvertently “run you off”. Now, one last warning: on the long run, a crystal meth addiction will be cheaper than sailing. All your family and land friends will begin to wonder about you – and don’t be surprised if they try to stage an intervention. Be forewarned, all your new sailing friends are actually co-enablers and dependants – last warning.
Most of us “old timers” have spent a lot of time in different sailboats so we know what works for us, what our aspirations are. Everybody is different and what may work for me might not work for you. My MrsB is fond of saying “boats shrink a foot for every week aboard”. Bigger is generally better until it gets too large to handle comfortably (think about your spouse). For example, the primary winches on my 34 are 44s, they are 72s on a 44 footer. MrsB’s abilities max out at the 40-42 foot range. We have some retired friends who spend the winters in Mexico on their 36 footer (and summers travelling the US in an RV). We don’t know how they do it. Our 34 is borderline too small for what we want to do. What size gets you is more tankage, longer “legs”, more storage, and more comfortable living space. The downside is price and operating expense increases geometrically as LOA increases. They also take more to sail. For example, the primary winches on my 34 are 44s, they are 72s on a 44 footer. MrsB’s abilities max out at the 40-42 foot range.
Sadly, economics and budgets will be your deciding factor. Despite what we enablers might say, sailing and cruising will cost a lot more than you first imagine. There are no free rides, better boats cost more. Decrepit ones break down more. You see a lot more of the latter in the marinas of broken dreams. Captain Ron and Summer Rental are just movies, not real life. Don't think you can buy something on the cheap and turn it into a first class boat with just a little paint and elbow grease. Most people who go this route end up spending way more than what they would have done if they bought a bristol boat in the first place. Don’t be undercapitalized.
Amount of time motoring is subject to a lot of variables, wind, no wind, wind on the nose, etc. It is also dependant on other factors such as type and condition of your boat, and your sailing abilities. Schedule comes into play too – would you rather be bobbing around or in the next harbor where there’s ice for your drinks? For what it’s worth, on the long haul, we do about 20 percent motoring. But I’m also a racer and certified string puller so I can eke out more speed (and distance) than a rank beginner.