1. If you are talking about 2 months worth of supported tours, I wouldn't be surprised if you ended up speding more money going that route than you would buying the gear you need for a self-contained tour, especially if you do a camping supported tour, since you would generally need a tent or some other shelter, sleeping bag and pad anyway.

2. Whether or not fully supported are worth the extra cash is entirely dependent on you. The differences are mostly one of convenience. Route mapped out and maybe even marked on the ground. Food and accomodations arranged fror along the way. SAG service. Luggage transport. I have done both supported and self-contained tours. I enjoy the latter much more for the reasons already noted, but I won't automatically eliminate a good supported tour from consideration.

3. Without knowing exactly where you are and how far you are willing to travel (travel cost is another factor you must consider), it's difficult to recommend specific events. I have done three Cycle Oregons and consider them extremely well run and well supprted, and the routes have always been stellar, if you can put up with oover 2,000 people for a week, that is. But don't look at that for this year since it sold out in about 2 weeks. Maybe you can get a copy of the Cyclist's Yellow Pages from Adventure Cycling Association (they also run supported and self-contained tours). The Yellow Pages contains a wealth of information about cycling tours, touring companies and events.