Sailing is a pastime that can be experienced by anyone who has the desire to experience adventure. I would recommend a year's sailing to almost anyone. Learning the basics does not take too long. Understanding how too prepare a vessel for sea is quite straight forward. Yes, it takes a bit of time and it also can cost a bit too, but in the grand scheme of things it should be factored into the adventure.
I think the most important thing that I ever discovered during my sailing career is that whatever the so called experts say: Your decision is what matters. You are the one who will be on the ocean. There are many ways of doing things and there can be many "Right" answers, but the decision is yours. Look for the answer you are happy with. Listen to the experts and learn, but you must ultimately decide what is right for you and your crew.
When choosing a yacht, budget is one of the most important considerations. Remember that no yacht is totally ready for cruising. All vessels need preparation and customisation. There will be a learning curve.
What can I add to what has already been said? Choose the yacht that will fulfil your current sailing ambitions. Choose a yacht that you like. Don't over extend yourself. Be realistic. Plan an exit strategy. Consider the additional costs of ownership very carefully. Then just do it. Fixing up a vessel needs be carefully costed as chandlery and labour costs differ greatly from country to country.