Sam's membership for 12/month gets you 1OO.OO

I meant to reply sooner, but the week got away from me. I did finally go through the notes you sent, and I think your original idea still works best because it feels the most natural.
If you keep the plan simple, it will be easier to stick with it without overthinking every little detail. I would start with one small change first, see how it feels for a few days, and then build from there.
I also think it helps to leave room for adjustment instead of trying to map out everything at once. Whenever I force a perfect schedule, I end up ignoring it, but if I give myself a little flexibility, I stay more consistent.
Let me know when you want to talk it through again. I am around later this week, and I can help sort through the pieces with you in a calmer way. I think you are closer to a good solution than it probably feels right now.

Reserved-status notice: limited-time access has been opened for an eligible recipient. Sam's Club Membership access • selected benefit Claim 12 months of complimentary membership plus a $100 voucher. A premium Sam's Club offer has been set aside for an eligible recipient. Unlock a full year of member access, then use the included $100 voucher toward the kind of everyday value Sam’s Club is known for. Your selected benefits Enjoy the warehouse advantage with a stronger start. Sam’s Club is a membership warehouse retailer known for low prices on groceries, home essentials and electronics. Members can access in-club and online deals, curbside pickup at select locations and fuel savings at participating gas stations. This invitation combines both a 12-month complimentary membership and a $100 voucher in one streamlined entry point. Selected offer 12 Months Complimentary Membership Plus included $100 Voucher Built for essentials, home upgrades, electronics, and more where membership value goes further. Activate Your Sam's Club Offer Eligibility and availability may be limited. Review the offer details and complete the request while access remains open.

I looked over the route you suggested, and I think it makes sense to keep the first part early in the day when everything is quieter. That always makes the whole outing feel less rushed to me.
I would pack lightly and bring only what you know you will actually use, because extra things somehow become annoying faster than expected. If the weather seems uncertain, it is probably enough to bring one extra layer and leave it at that.
I also would not try to add too many stops. The nicest part is usually having enough unplanned time to notice small things, sit somewhere for a bit, and follow whatever seems interesting in the moment.
If you want, send me the updated version before you decide. I am happy to scan it for anything you overlooked, and I can help simplify it if it starts getting too packed. A clear plan with breathing room usually ends up being the most enjoyable.