I personally like kick starting, probably because it makes me FEEL cool. But honestly - who cares what people think? Well, I guess a lot of people care, which is why so many people buy big HD's.
As far as the original question - I agree with riding the bike until you get a feel for what needs to be done. Valve adjustments are easy. Once you get into the carbs, it can be a lot of work, and you have to be thorough, but anyone with good mechanical sense can do it (including sync). If you're willing to live with a bit of oil leaking, then don't touch the engine. But if it gets bad, then you should take the plunge and do it yourself. It's rewarding to ride something that you've worked on yourself. Just takes patience.