Paying others to fix/ maintain your boat is definitely one facet of what is expensive about owning a boat.
Keeping your boat moored or docked for a year will totally crush the pittance that is redoing rigging however. My point being- buy it, do what needs doing- sail it - and get shed of it. Until you get the itch again. Buying and working on boats IS the cheap part of ownership.
As for the old folks at anchor etc-
Absolutely, I didn't teach myself to sail- my dad did, you needn't be a rocket scientist to recognize the value of others experience. Additionally- I'm just a service oriented guy. And now that I can't serve my country- it's all about the individuals I run across on a day to day basis- and the 60-70 something set, who can afford more boat than they can handle or fix are without a doubt the majority of who I run into on the hook. That said- it's about all that makes me feel like I'm still relavent when I can help them out- or even just hang out for a few and make them feel relavent. Like John prine said "hello in there"
I'm single handed about 90% of the time on my boat- so a little company is always welcome respite- and while I always shocked at the overall lack of seamanship I meet- I feel no need to be critical of others out there- like DR (initials right?) said- at least we are out there. It's important to be thankful for the experience and knowledge I have - and it's dead wrong to refrain from sharing it and learning from others.
It's often times however that ghastly handholding motor sailing mentality of the group that is a turn off. That and the idea that we can't cast off or pull anchor if there's more than 8 knots of wind. Oh- and the mentality that if you have to tack a couple times to get there the weather is "bad"