Thanks for sharing the details.I have two pairs of 4497 boots and two pairs of 2298 shoes and one pair of 325 shoes.
Where I'd say 4497 is a perfect fit for me, the 2298 is definitely narrower in the toe area. Also the heel seems somewhat more loose in the 2298, but that may also be due to being shoes instead boots.
Being somewhat critical I would rate the 4497 an 8 or 9 for my feet, and the 2298 a 6 or 7. Don't know about the 4444 last since I'm not sure if sizing down would fit me, and I'm not a huge fan of the chunky Bourton aesthetics or believing they offer something completely different compared to my Stow's. I'd prefer Church's Grafton's, C&J Pembroke's or something like Tricker's Daniel/Richard/Robert in the case of shoes.
I have an UK10 in 2298, 4497 and 325 and wouldn't recommend sizing down. The 325 and 4497's fit about the same (both are favorites), with the 325 maybe being a hair snugger. The 2298 is best if you don't require the added width in the toe box.