That's such a personal choice, you're not gonna get a simple answer here -- unless you can trust complete strangers to have the same preferences you do. All we can do is point you to some factors to consider.
It's like asking "Should i buy frozen lemonade, or should i make my own?" "Hire someone to paint the fence, or do it myself?" Depends on how resourceful you feel, what gives you satisfaction, what you consider work vs. fun.
You have 4 choices, as i see it:
1) Tour companies. These are catered vacations,, they take care of all your needs (for a hefty price); they have to gear toward the lowest common denominator of the group, they focus on comfort and amenities rather than exploring. Best choice if you like comforts and luxury, and need company.
2) Get a friend, or small group of friends, to make a summer of it. Especially if one of the friends has touring experience. The best way to explore touring, especially if you doubt your preparation and bike maintenance skills -- like any other activity, you learn the ropes, share the tasks, and have others to fall back on.
3) Adventure Cycling Association (www.adventurecycling.org
) has well-organized fully-loaded "independent" tours. This is like a combination of #1 and #2, and you have a professional leading the tour to learn from. ACA is an excellent resource for touring info. Their tours are also expensive, and some people find they can't handle the 3-month (or whatever) commitment to the group.
4) Head out on your own. If you've prepared and you like to be alone, do it yourself. Maximum flexibility, no contraints on your pace or direction. But some people can't handle days of solo riding.
Going solo or with friends, you get to choose: loaded touring, or credit card. Another basic decision.
Mass rides like RAGBRAI are rolling parties
, and you learn if you can do big mileage and spend multiple days in the saddle. But they're most like touring companies (#1 above). It's a huge leap from there to loaded touring. The best thing you can do is to take a few weekend (or 1-week) trips as shakedown tours, to check your enjoyment factor, learn what to tweak, find out what works and what doesn't. After a few of those, you'll be ready to head out on your own (or not...)