As far as I can tell, all Firewall and other rules are the same on both. The only difference is that the laptop with the connecting wallet is running Windows 10, the one that won't connect to the Bitsend network is running Windows 8 (everything else works fine except the Bitsend wallet). What am I looking for in debug.log? It's very long... I apologize, but I'm not very "tech savvy" with this kind of thing. I just figured I could download it and run it without issue like I did on the other laptop.
There's should be no problem to run wallet on w8, someone else need to test it. I dont have one.
About debug.log - rename debug.log to debug.log.backup and start wallet until it fully loads up.
Then open debug.log and trace if it contains errors until "GUI: PaymentServer::LoadRootCAs".
After this point wallet should receive messages from bitsend network.
If you dont get what happening, you can post .Log here, or somewhere else, but make sure you clean personal data from it. (like your IP and stuff, you can use "Replace" feature in notepad)
Also, check if peers present and OK in wallet's settings->debug->peers.