Advice please for multi trips in 2021

[Brewers]

Hi all, my partner & I were intending to have x3 1 week holidays in 2020, the first being in May. We are now resigned to not having a holiday in 2020.

Following a DIBB tip off, we have booked a trip in Feb 2021 & we are also committed to an August 2021 trip with my kids. Here are the plans so far:

Feb 3-17 fully paid £1220 for 2 adults, direct Virgin flights from Manchester, 14 nights basic accommodation at Baymont Inn & Suites Celebration, breakfast included, with return coach transfers from airport to hotel. I looked at booking each element separately but could not do it with much price difference.

Jul 27- Aug 12 our preferred villa already booked, nothing else organised as yet.

My questions I'm seeking advice on are:

1) Would these 2 trips alone be enough to get value out of annual Disney & Universal passes? Or would I need a cheeky birthday trip in December to see Florida at a different time of year ?

2) If so, what's the best way to get them, buy them up front or upgrade 14 day passes when there?

3) If we get annual passes would this include parking, which might make it value to add car hire in Feb (we'll definitely have it in Aug)?

Any advice, as always on here, would be greatly appreciated, thanks in advance.

[MENTALMUM]

I upgraded my 14 day ticket to an annual pass last October, it was £592 approx ( sorry, cant remember exact but about that) to upgrade, they took off the cost of my 14 day pass and this was what was left. I upgraded at Disney Springs on my first day in Orlando, I believe you could shop around at the resorts as the upgrade price can vary. While we were there we visited the Disney parks for 10 days so that was no parking charges for that time. You also get 20% off merchandise which I bought far more than I needed but 20% off it all, there is 10-20% off food, mainly sit down meals but 20% off Joffreys coffee.
I should be going in April but that is sadly looking like a no no for now, if we had gone then I had a few days planned, no ticket or parking to pay as its included in the annual pass. I still have a trip in September which I am hoping will still be going ahead, again annual pass covers the cost of a ticket and parking included before I look at anything else.
The only down side it that you can only book 7 days fast passes, you can add another day every time you use a day but this wouldn't work for everyone, its fine for me.
You have to balance out what you would pay if you went twice or more paying separately against the cost of an annual pass ( you can find the price on Disney website). If I manage to get back then it will be worth it this year but I do believe prices have gone up.
Unfortunately the issues with Corona have put a dampner on my travels but I would definitely consider getting another one if I was going more than twice with the time frame.