This is based on 7 TGO challenges and Pennine Way and a few other things...although others will probably have differing views on some things -but these are my thoughts on your questions.
1) Dont worry about speed (although 1.5 to 2 mph would be normalish with a heavy pack). Take your time and have things like tea bags and your cooking stuff all really handy so you can stop and have brews. 30 Miles seems a long way, but I suppose it also depends on how much uphill work there is on that day and what the paths are like. Dont worry too much if you dont manage the whole 30 (I'm not suggesting that you're not capable of this by the way - its just that sometimes things dont always work out) Just be ready to be flexible and dont get ruled by your initial plan. You have to relax - its a holiday.! I tend to walk from 9 to 5 - or 6 if I'm late and have lots of stops - elevensies for bacon and tattie scones, lunch if I get hungry, afternoon tea and biccies and snooze, one or two extra stops to build up strength for my main break - that sort of thing - you get the idea, I'm sure.
2) There's loads of boil in the bag stuff from wayfarers etc - which I sometimes use. I'm specially fond of the chocolate sponge, but the treacle sponge is like an ice hocky puck in sugar (shudder). I also use supermarket b-in-b curries - a bit heavy to carry, but they feed two (i.e. one greedy/hungry person) I cook on a tiny Primus and with the curries, I cook a packet of microwave uncle ben's rice (just add a small amount of water, and when thats cooked, i add the curry and mix it all together and tghen stuff it down my face. You have to wash up after this, obviously, so I take a little pan scourer/sponge for that.
I also carry things like cracker barrel cheese and oatcakes, and porridge.... getting hungry now...
And I have a supply of approx 50ml of rough scotch (eg bells) in a cycling bottle for occasional night time celebrations...
I think wayfarers stuff or army rations are OK - but never just quite enough for me as I'm a pig.
Sometimes I would take just one self-heating meal as a back up incase of stove trouble. Probably not so important on NYM
3) People can carry different amounts depending on their own physical attributes and, to some extent, what they do for a living - but I find that if I can get a base pack weight to about 22 pounds, or less if possible, then thats manageable, and not very noticeable after a while. You'd have to add food to this, and , I would guess on NYM in summer, some water, which is quite heavy.
4) I'm not really up on jackets - I've got a Paramo with lots of vents and zips, so you don't need to take it off. Ever!
5) Never been to Filey! But happy birthday anyway.
One of the ways to reduce pack weight is not to take too many spare clothes. Its possible to post yourself a set of clean stuff to the post office at the end of the walk - address it to yourself post restante. If you're wild camping, it doesnt matter too much if you stink a bit - and on a five day trip, you'll probably just be starting to attract the attention of dog foxes, lovesick badgers and pubescent stags- so be very sparing on what you take. Smartwool base layers and socks are quite good for this sort of thing.
Its going to be fab!