KWOOD,
I just want to mention a few things. The bench you have is nice and sturdy and will work great. I have one, not for handloading but for my cleaning bench and I like it. The one thing I don't like about it is unless you modify it the lower shelf isn't strong enough to hold much weight. If I didn't already have a solid bench I would however consider using one for mounting my presses. The drawers are nice, not very deep but still useful.
I would say as a friendly suggestion is to consider getting a press mount such as the inline fabrications ultra mount. This will allow you to mount the press on the leading edge of the bench and also let you access the drawers. It also will raise the press, depending on which model mount you purchase, from between 4 to 10 inches. I think you will find the configuration you have uncomfortable especially if you stand while you handload. Personally I like to stand, I'm 5'6" tall and have found out through a lot of trial that for me the press base should be 49" high. I achieve this by having my bench top 39" high + 10" thanks to the ultra mount. The Windsor bench is I think 32" high. You are not me of course, I get that.
I have a hutch on my actual reloading bench. I think they are a good idea. Looking at yours my opinion is that you will find that it isn't robust enough for the task. I would suggest a plywood back and if you really want pegboard mount it on some kind of standoff but I think you will find that hutch swaying in the wind and annoying. I also have heavy duty "L" brackets that steady and tie the hutch to the wall. I might also add that I have 1000+ pounds of ammo and bullets on the lower shelf of my bench and even with that kind of ballast I still need a solid hutch that is really well mounted to the bench top and then as mentioned I use the L brackets to add additional stability. Having a solid non-movable bench that is comfortable is just as important as a good press and die set to make handloading an enjoyable endeavor. This has been my experience at least.
The suggestion to ditch the casters I think is a good one. Most of us have space issues, I know I do, but I also have experience that has taught me a few things. Please don't take any of this as a personal insult you obviously have some woodworking skills and have given this some thought .