Hello again i have just measured the handle drop on my pink Bayswater and it is 8 inches
From the highest point of the shoulder strap to the top of the bag is 6 inches the additional 2 inches is allowing for where the handles are attached to the bag. When i wear the Bayswater on my shoulder it fits great with at least 1 inch gap between my arm pit LOL and the top of the bag... hope this helps
Only a fine wear one (mac etc) thick like wool and the Bayswater does not sit on my shoulder correctly... My advice would be to go and try the Bayswater on your shoulder and in hand and see how you feel with it
I have a python Roaxanne, an oak Blenheim, two Aylers, 1 pink Bayswater, 1 red Bayswater , 1 oak Bayswater and a few older styles so 11 to date if you are serious about selling the Rosemary PM me i can't resist Mulberry
Both are roomy and easy to carry or wear on your shoulder . I have 3 Bayswaters 1 is oak Darwin leather this marks easily and scratches but in my opinion it makes the bag look better
the other 2 Bayswaters are glove leather (1 red and 1 pink) so these do not mark or scratch as easily (i'm going to get 2 more this week (possibly vanilla and chocolate i'm not decided yet 
) With the Roxanne as it is python skin it is delicate but i only use it for special occasions so it is fine and i never put it on the floor it stays firmly on my lap I would say to you to try both bags on yourself so you can see which suits you the most . I also find with the Bayswater (2 of mine do not have the padlock and simply fasten with the postmans lock ) but the oak has the padlock and i am not brave enough to leave it open incase i lose the lock , so it can be a pain getting in and out of it having to undo the lock all the time.
