You've gotten some good suggestions here already, particularly regarding the new snuff suede wingtip boot from Epaulet. I have a pair of those headed my way and looking at the stuff you list as already owning, I think they would make a good addition you your collection as well. I don't think there is anything wrong with having both tan and snuff suede and I think Alden's snuff suede is absolutely gorgeous.
Regarding the Roy Boot from Context vs the similar boot from TSM, I think the main difference is that the Roy Boot is on the Trubalance last and has dark eyelets and speedlace hooks while the TSM version is on the Barrie last and has brass hardware. In this instance, I think I prefer the dark hardware of the Context version. FWIW, Context has a batch of snuff suede Roy boots currently in production at the Alden factory - they were confirmed back in the fall and should be ready for delivery anytime now.
One other option that I would throw out there is the unlined suede boot. I think the chukka boot in suede is an entirely different beast than the shell cordovan version. It's so much lighter and more comfortable. I live in mine in the summer.
Many thanks for the suggestions. As for the unlined Chukka, I have a cxl one. Do you think a suede one will serve me better in summer, and how much is the difference?
Alden x anatomica. These fit larger than other modified last shoes I have that are the same tagged size. Works with thicker socks but a bit disappointing because the modified last shoes I have are easily my best fitting Aldens