They are going to have to address the shade (or lack-thereof) issue eventually. Also, this land has virtually no air conditioning with there being no store or enclosed quick service.
I hate to say it, but the land has all the makings of being legitimately dangerous in the summer. With people waiting in long lines in the sun, no AC, etc, I can easily see people fainting from heat exhaustion here and it being a big enough problem that we may see them at the very least put cover over the tables at Woody's Lunch Box.
If they do ever expand this land, i'm not sure more rides are needed as much as more to do. If they take down the two remaining (former) production bungalows, they could have enough room to build Woody's Round-Up, which could house an indoor M&G, a store, streetmosphere, a Saloon, etc. Any of that would be very welcomed and it would also add a lot better theming to the land entrance rather than just sort of walking in and seeing Woody.