Charlie,
More nice items. I think I can help a little with the Jay Publishing photos. I've done a lot of research on the Orioles photos and posted the Brooks Robinson photos in post #1149.
You don't actually have the 1958 Brooks Robinson photo. I pictured it a few posts ago. The ones you have pictured from left to right are 1961, 1959-60 (I can't tell the difference between the two years, if there is even a difference) and 1962. You will notice the printed name is different on the 1962. It's the font that determines whether it's type 1 or type 2. Checklists usually lump the sets into 1959-1961 and 1962-1965, but with a little work the years can be broken down. I picked up most of my photos in original envelopes.
Jays Publishing didn't print Baltimore Orioles, only Orioles, on their 1957 and 1958 sets.
Here are a couple more early team issued Brooks items, you might find of interest. They are generally considered 1957-59. The exact year is hard to determine.
1957-59 Team Issued Postcards
195759 Postcards 14 - Copy.JPG
1957-59 Team Issued B&W 8x10 Photos
Robinson, Brooks 1 - Copy.jpg Robinson, Brooks 2 - Copy.jpg