Hi there! :wave:
When I help friends plan their trips, I always ask, are you going to pick a dining plan? If so - then we pick which one works best for their traveling and vacationing style. For my DH and I, the dining is a big part of our trip. We love TS meals so we either get the DDP or the Deluxe DDP. If you are going out of pocket, then you can determine a budget and go from there.
As for how to pick what places? This part is fun! I'm a crazy planner with spreadsheets and the whole bit. So, we determine which parks we want to go to on what days. Then we have our traditional dining places (like Rose and Crown for the first meal and CRT for bfast on the last day). We try to pick 2 or 3 new places to eat each trip and then go for our faves. If you have not eaten at many places - then go through the menus some places you are interested in and see what you fancy.
Then...the 180 day out ADR phone call ( i know you can do them online but I am old fashioned! hee hee). I have my spreadsheet and try for the times and places that I want. I call first thing 180 days out and I rarely can't get the ADR's that I want. But if I can't get one - then either I go with my 2nd option or see if I can flip days around.
That is my madness! :lol: