We went in 2005 with Travel City Direct and it was cheaper than DIY. Began to get a bit nervous as it approached due to lots of horror stories, however here's our summary
Flight over fine - small delay which we nearly made up for in flight. Plane fine, a little older than eg Virgin, so no seat back TVs but legroom good, plenty of food and drink, helpful staff.
Car Hire arrangements fine
Small glitch at booking - had not got details right for son's girlfriend. Disney were great at sorting it out, providing temporary tickets etc.
Would definitely recommend staying on property. You don't realise the size of the place - you could easily be 30 miles out in a rental villa. But being on-site transportation etc is excellent. No real need to hire car, but I really enjoyed driving in the U.S. so would hire again.
We stayed All Star Movies - room fine larger than our travelinn but other than that quite like a travel inn with usual brilliant Disney theming. Did begin to feel a bit like a holiday camp at the end. Next time we plan to stay in the Contemporary as you can walk to MK. If you can afford I'd say its worth upgrading to one of the monorail resorts but not to one of the moderates.
On way back - long delay (8 hrs) but some people had been bumped from previous night. Travel City dealt with it fine. Let us know from the start gave meal vouchers. However, this is where they fall down. As they have a small fleet if one goes wrong you're stuffed. Unlike a bigger operator that has another plane to draft in.
On balance - although we don't have a TCD horror story, next time I'd DIY - book hotel etc. with Disney direct and flights prob with Virgin
Hope this helps
If you want to ask any other qs about booking, restaurants etc. let us know - know what you mean about size of WDW boards
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