The airplane you buy depends on more than numbers; it should suit your personality, physique, skills, age, and above all it should meet your standards for the kind of equipment you use in life.
All that aside, it's a noble goal to fly yourself, and learning to fly is a great idea for fun, but owner-pilot GA is obsolete as personal transportation on the east coast.
If you read Flying magazine, check into the experiences of Richard Collins and Dick Karl. They pretty much exemplify the kinds of missions that owner pilots like to think themselves capable of flying, and that, back in the day, made a lot of sense. They're both selling: Collins sold; Karl should have when he had the chance. I sold mine last month, after years of doing exactly the missions you are talking about. It just didn't add up anymore. In fact, strictly speaking, it never made financial sense; but now, you have high fuel costs, Lockheed-Martin corruption and ineptitude, unreasonable airport fees and policies, insurance costs (which frighteningly enough represent the real actuarial risk of the GA enterprise), crazy hangar costs, airport "security", nonsensical routings, TFRs, the NOTAM system from the 1850s, and in general the joys of dealing with a U.S. government that acts like the Cowardly Lion.
Let's just say that if you're on the east coast, you're better off with a fractional. A Pilatus would work nicely....