The only thing I’d add to previous posts is: the stretch from just after Side Farm to Howtown is very much not a nice, easy stroll by the lake - it’s a surprisingly tough walk compared to how it appears on the map.
Yup, I was thinking that when I said Glenridding (or Patterdale) anti-clockwise. You get the Side-Farm to Howtown section out of the way first - then decide how you're doing time wise. If you want to save time just get the steamer from Howtown to Pooley and then continue south on the easiest part of the 'Way'.
That said, the route from Howtown to The Cockpit then down into Pooley is a lovely walk with nice views of the fells so I'd always take that instead of the road route - with the ramblers bar at Howtown about the only drink/food stop you'll get till you're at Pooley.
Western side - Airy Crag is (imo) the easiest peak to bag all day and well worth it, you can follow the route down to Aira Force which is a nice change of scenery, and probably easier than the route down Hind Crag if you take the route around. From then onwards you've got a couple of hours of leisurely walking with lake views - Patterdale car park is £6 a day I believe so would be reasonable, and if I was being civilised I'd book a table somewhere to restock on those carbs.