@jmaxwellUSAF whether you redistribute a summary /24 for the anyconnect VPN network or hundreds of /32's to the adjacent network devices, they would be pointing to the same destination (the ASA), so it doesn't matter which is preferred. The only benefit of a summary route is you don't have hundreds of /32 in the routing table of adjacent network devices (assuming you don't redistribute the /32s).
If there are no anyconnect users connected to the ASA but there is a summary it's still unlikely there would be traffic destined to the anyconnect pool network routed to the ASA in the first place.
You could always specify the interface as null instead of outside, so therefore anything routed to the ASA that does not have a connected anyconnect user would be dropped, if that is a concern.
In short, removing that static via inside interface resolves your initial issue or recreating that route via outside/null also resolves the initial issue.
