I completed all 214 Wainwrights a few years ago. Took a little under two years IIRC. Did them all in day trips - could have done them a lot quicker with a few long weekends.
I know a lot of people frown on 'bagging' but it's a great way to get to know the whole of the Lake District.
Towards the end it became a bit of a chore and I looked forward to finishing the list so I could just be more creative in my choice of walks.
First one was Coniston and the last one was Yewbarrow (a great one to finish on - careful on the descent).
Obvious highlights include Striding edge, Sharp Edge, some of the lesser known routes up Scafell, Pillar... (Too many to mention really).
Wainwright described his seven guides as a 'love letter to the English Lake District' and the books are a fitting tribute to a wonderful place.