Firstly, there is no alcohol in the mash tun so it can have no effect on fittings/plastic. No magic happens until the yeast get involved. And infact, nothing needs to be sanitary on anything before the kettles valve as the boiled wort is on it's way out.
Forget the sight gauge for the mash tun, it's useless. Once grain is mashed in the whole level thing changes anyway, and plus if you transfer 20L of water from your HLT then you know that there is 20L of water in your mash tun. Why do you need to measure it twice?
You miss the point of a sight gauge with your question asking if it matters if you use a tee joint before the ball valve on the HLT. As someone above said, once you start drawing liquid through that valve your gauge level will change. This level varies depending of just how open the valve is. Once you start transferring liquid to the mash tun how do you expect to actually read how much liquid you have transferred-the only way to get a reading is to shut the valve. Why would you want to do that if you could install a sight gauge on it's own dedicated fitting and actually use it to monitor volumes as they transfer on the fly accurately-without having to shut the valve to take a reading.
The pump vs water level issue is still a valid issue if you pump from you HLT. Not everyone uses gravity to transfer from HLT to mash tun, and even if you do use gravity the problem still exists.
My recommendation is to really think about what you "actually" need and think about why you need it. Dont just blindly copy what other people did, think about what you want to achieve, why it's important to you, how is it going to work best in your situation and then how is the best way to do it. Once you start doing this you can work out what people have done wrong in their systems and how you can do it better. There are so many copied mistakes out there because people just copy what they have seen without actually thinking about it, and the cycle continues.
It's worthwhile having a good think about things before heading off and do it.
Good luck.
Cheers, Justin.