Sure Stack upgrade required all the switches to reboot.
If you looking high availability, then you need to build 2 Stacks to connect to buildings, that add up the cost.
If you do not like to add up the cost, then you use Layer 3 P2P with OSPF so failover will help you for redundancy, If you looking Layer 2 only then you can think about loop avoidance making a right decisions. ( Traditional looped design with VLANs spanning access switches - below document)
Again this suggestion based on your information my views - so suggest to make small diagram for reference or refer the CVD :
https://www.cisco.com/c/en/us/td/docs/solutions/CVD/Campus/cisco-campus-lan-wlan-design-guide.html