We stayed off site in a timeshare. It was a huge mistake for us. We assumed that Calypso Cove would be a nice property because our timeshare company recommended it. Huge mistake!! Hands down the worst place I've ever stayed. We decided that we would never stay off site again.
Besides the awful accommodations, we felt like we spent quite a bit of time in the car and driving through traffic. Plus paying for parking every day. It also was not easy to go back to where we were staying midday for a rest. Once we got back, we stayed put. It just wasn't convenient.
That being said, I have heard people complain out how long it takes to use Disney transportation. So, maybe driving to the property and paying for parking wasn't so bad after all.
Definitely use the Fast Pass system. If you have the Disney app you can even manage them from your smart phone. I didn't really like planning too far ahead, but our experience did get better when I got Fast Passes at least a day before.
We made the mistake of going to Magic Kingdom on our first day. It was totally overwhelming and even now, 4 months later, if you ask my kids they have no desire to go back there. But they loved all the other parks. If we had it to do over, we would have done one of he smaller parks first. I think that would have helped us feel a little more comfortable wit how Disney works and we would have enjoyed Magic Kingdom a lot more.
Another plus for me, was that halfway through the week we took a day away from Disney. But we didn't do any of the other Orlando experiences. Instead we drove down to the Kennedy Space Center for the day. It was a nice break from the Disney overload and one of my favorite parts of the trip.
Even with all of the reading and planning I did, I still didn't feel prepared do the trip. Try to just go with the flow as much as possible and have fun.