Great thread, OP! Every single trip has been SO different for me, I don't really have a set way of doing things - I love trying out different strategies or just changing up my speed! I'll also include my
Disneyland visits because why not. But in general...
Who are the travelers?
I'm the only consistent person! Mostly I go with close friends, except one trip to WDW with Dad, cousin and uncle, and 2 trips to Disneyland with Father, Mother, Aunt(and also a close friend!)
When do you go?
Whenever my schedule and finances allow it! I haven't gone at the same time of year yet. I've gone end of August, Beginning of May, Mid April, and early October. at Disneyland I've been in August and September. I would like to try all different times of year, this year I will be heading with BFF and her Fiance in late November to experience a Disney Christmas!
How many days?
Always a week, 7-8 days besides my first trip(We only did 4 days and I learned that it was nowhere near enough!). I've never been on ANY vacation longer than a week other than when I went to Europe. I would love to do Disney for 10 days, I think that amount sounds perfect, but scheduling and finances have yet to allow it.
For Disneyland, 3-4 days. I could stay longer but I think between 5 and 7 days would be enough. 3 to 4 days is still a lot of time to get stuff done there!
Onsite/offsite? Resort Level?
ONSITE!! I would sooner put off a Disney World trip for later to save for onsite. The total immersion is a huge factor for me, and planning and getting around is so convenient. The hotels are so fantastic and are just as essential to my vacation as the parks.
I love Value and Deluxe, Value for the outrageous themes and prices. I can't say enough about how much I like the hokey over the top themes hahaha. I also love Deluxe, the location is fantastic and you just feel all the energy of the parks all around you. I also have expensive taste for a person with no money!

I like to feel pampered and I like the extra amenities. I would like to try staying in every single resort at some point, though admittedly the Moderates don't appeal to me. I don't really get the point. Tried POR a couple years back and wasn't impressed. I do want to stay at CSR at some point, maybe after all the construction is done!
I have only stayed onsite at DLR but I don't think it's as necessary there. I love the hotels there and will probably continue to stay in them, but if I lived closer to DLR and could go more often I would probably be more flexible.
Car or Disney transportation?
DISNEY TRANSPORTATION! I don't get all the Disney Bus haters on these boards, I love those magical buses. Maybe i've been lucky too, but I've never had to wait too long for a bus except at park closing, which is to be expected. The boats and the MONORAIL OF COURSE!! I drove my car to Florida for our POR trip, but I just parked the car and didn't look at it til the end of the trip. I may try to do this again for my upcoming trip. It was nice being able to buy souvenirs and not have to worry about whether it would fit in my luggage or would be contraband. But I have no interest in driving on a Disney Vacation.
Disneyland, this question is irrelevant. Everything is in walking distance of each other, though the monorail is always fun and worth a ride(though it's honestly totally unnecessary). I actually enjoy the monorail in Disneyland a lot more as a ride, the views you get are SO cool, and as of 2015, you could still ride in the front with the driver! It's way less of a big deal there, if you want to ride in the front you just ask and hop in.
Dining: plan (type) or OO
I have done OOP for all but one trip, we got QS free dining. I loved it! Not having to budget for food and having all those extra snack credits was awesome. I am considering doing DP for this trip. Not sure if I would go for regular DP as it has gotten so expensive(though I do have some TS i'm dying to try), but QS I would consider. I love to eat and not having to think about food money makes the trip so much more relaxing.
Daily schedule: RD or sleep in? mid day breaks? pool days? touring plan or go with the flow? park hop? meals? evening plans?
I am a morning person, and like to do RD most days with maybe two days to sleep in and take a break. I like to do a few days where I'm at the park open to close, but definitely have learned that I need a couple days of NOT doing that so I don't burn out. But yeah I can do the parks all day most days no problem. The days I don't RD we usually hang out at our wonderful resort or do Disney Springs or something, then do a park in the late afternoon into the evening.
I HATE midday breaks and park hopping. Both are huge time wasters to me. The amount of time to travel back and forth makes no sense to me when I could take a break in a nice restaurant. I do LOVE the well themed restaurants, don't need to do one every day but I do like a few per trip, usually on the days we go open to close because, again, I HATE MIDDAY BREAKS!! And park hopping just seems overstimulating. When I am in a park I want to enjoy it as much as possible and appreciate the little things. i tried park hopping from AK to DHS last time and just felt burnt out when I got to DHS. Did one ride, shopped a bit then just went back to the resort to relax. Felt like I wasted an afternoon. The only time I have utilized a midday break was staying at CR in August 2010, we would bounce back and forth between CR and MK. I would do that again because you're not actually leaving the area at all, LOVED the location of CR.
I have never dedicated a whole day to my resort. I never travel with kids so I don't need a WHOLE DAY in the pool. I usually take a half hour dip or something. I love spending time at my hotels, but over the course of a week spending a few mornings or evenings there has been enough time to explore everything.