As to performance.. with tap your going to see all the broadcast traffic since your L2.. So all devices on both sides will be sending your broadcast traffic down your wan connection. Which is normally a limited pipe that should be used to carry useful data not every client broadcasting for wpad, or all their UPnP data - all the noise that your typical device sends out.
Since it Layer 2 you will also have all the ethernet overhead on all traffic going over the tunnel.. Is that at a basic enough level for you to understand?
"I've found tons of people who have site to site VPN's via tap and are bridging their networks"
I don't doubt it - there are lots of people that just don't have clue one to what they are doing at all.. And don't even understand what they are working with and why it doesn't work. They just know that hey if I use a tap it works… There are a lot of people in the world that have to think rabbit through the hole when they tie their shoes ;) hehehehe
"Several of the resources that are being accessed have software firewalls that are configured to only allow the main subnet (192.168.1.x)."
Well the proper way to solve that issue would be to adjust the firewalls to allow the traffic you want and desire.. Not just blindly trust traffic because its on the same natwork? If you want to allow port xyz, then allow that from your other sites machines either by specific IP or by the remote network address space as source, etc. Another way to work around that issue would be to nat your traffic over the tunnel so it looks like its from the same network ;)
So these devices are going to directly connect into your vpn server? Or your going to do a site to site tunnel? So lets go back to your "to only allow the main subnet (192.168.1.x)." So these clients already have an IP on 192.168.1, and now you want them to connect to your vpn and also give them another 192.168.1.x address? So when they want to talk to a machine on the local network, how do they know to send it down the tunnel or just out their local interface? So you want to bridge these devices tap devices to the their local interface as well? Did you do that?
Connecting a site to site with a tap/bridge setup to extend a vlan is much easier to accomplish then client to server with client on the same local IP as the VPN via tap, etc.
As to openvpn gui being buggy.. I would assume its more you have not gone through all the steps in configuration of a tap setup, etc. Here is the thing while it can be done, normally it should not be done. The only valid reasons to have to use a tap would be if you have some protocol your running that is not IP based and can not be routed.. Your reasoning is that there is some software firewall that what you can not adjust? Who does?? Get them to do it if your going to setup a vpn from their machine to your network.