Microsoft is supposed to have either released, or is about to release an update for Windows 8 that brings back the Windows 7 start button and menu's so you may want to look into that. Here's a link to some info on the update:
http://www.cnbc.com/id/100844998
The wireless issue could be several things. Before doing anything else, I would look for newer drivers for the wireless device. If there are newer, definitely update them on the laptop and try again.
That's not too likely to be the issue. Encryption should not affect a wireless devices ability to connect to a wireless network. All it does is encrypt the wireless network to prevent intrusion or theft of data. WEP is old enough that it's easily penetrated with the right software. Maybe 10 minutes if you know what you're doing. WPA2 on the other hand is still a whole lot harder to crack. But I digress.....the problem is connecting to the network itself and encryption should no be able to prevent that if you know the correct encryption key (WLAN password).
If you're buying a new router, be aware that
all your devices will have to connect manually (the first time) to the new WLAN (wireless local area network) even if you use the same SSID and encryption key. It's a new router and will not be aware of existing wireless devices (like smart phones, pads etc) that have been connecting to your existing WLAN.
If you'd like a hand when the new router arrives, let me know and PM me your phone number. We'll arrange a time to hookup on the phone (I have unlimited long distance in north America so I'll call you) and I can walk you through it if you need help. I suspect you won't, you're pretty tech savvy and a SOHO router isn't that complex. Just remember to use WPA2 - personal encryption when configuring your WLAN. I would suggest using the same SSID and password just for the sake of simplicity.