Its a big adventure attempting your first LDWP, especially one as long and challenging as the 267 mile long Pennine Way, but a friend some years ago, took all the pressure off themselves, by hiring the services of a company who did all the accommodation bookings, food, and transportation of baggage throughout the walk.
Wild camping, cooking your food on a stove, and all its associated thrills, has one big advantage if your fortnight's weather remains dry and favourable, it's an adventure holiday you will never forget, but as we all know, the British climate is so unpredictable, and the central spine of the Pennines, attracts some ferocious conditions, and September is rather late in the year, though weather can be very settled that time of year, but daylight hours are that much shorter.
Granted, having a small privately run company take all the associated pressures of things going wrong, is not to everyones taste, but you will still be doing the physical walking, but your accommodation, food, and carrying of baggage will be handled by someone else, which is a huge incentive to book their services.
The owner of the company arranges to collect the walker at a designated point, with warm clothing, warm food, and plenty of encouragement for the weary traveller, but that takes away the adventure of doing it solo, and may destroy the whole experience for some walkers.
Knowing what to take, and leave behind, can only be learnt from past experience, and the carrying of a very heavy sack on your back for mile after mile, over desolate countryside is a challenge in itself.
Many people here, will have completed various LDWP numerous times, and know what to take and leave behind, but as this is your first attempt of the Pennine Way, you may not have considered the services of a company who do all the background work for you.
Which ever way you plan to do the walk, good luck.
If you have set your heart on doing everything yourself, then i am full of admiration and respect, but having the journey of a lifetime fully mapped and taken care off, by an experienced person, may guarantee success on such a long challenge walk, and its not as costly as you would imagine.