I see a couple of things, which may not be the main issue, but could certainly be contributing to it:
Both sides are double NAT'd. Not ideal, but also not a big deal in and of itself as long as there's awareness of it and you have access to the edge device if an issue presents itself
The server-side LAN is 192.168.74.0/24, but the client is routing 192.168.0.0/16 over the tunnel. This overlaps the server-side WAN subnet and is undoubtingly causing an issue of some kind since the server's WAN IP is 192.168.74.74. At a minimum, the client-side will need to modify the IPv4 Remote network(s) line to the correct server-side LAN subnet. Worst case, the server-side may need to assign a new LAN subnet if there's overlap somewhere and then adjust the config accordingly.
The client-side WAN IP is 10.74.1.74, but the server-side is routing 10.74.1.0/24 over the tunnel which is the client-side WAN subnet. Why are we routing the client-side's WAN subnet over the tunnel here? This should probably be removed.
Other things to look at:
Verify the IIS server is using PFsense as the default gateway
Verify the client-side's DNS is resolving the hostname to the correct IP