My name is also Chris so I had a slight chuckle at that.
Mental health still has lots of stigma, tread carefully if/as you mention it to them. I've been openly told by a few they think I'm mental, intended as an insult but then followed up when I next saw them with an explanation about me being on the spectrum. It's offensive if it's said accidentally as an off the cuff insult.
The next question or point that follows is almost always professional help. As someone in that situation if you are aware then you kinda look forward on a future that could be regular interaction with mental health professionals for the rest of your life, it's a scary idea to think of.
Be aware that whatever you say might also bear no fruits, and even have a crushing response like "I know, so what".
The ripped clothes and shoes thing I totally get, for a while years back I did the same and in the grand scheme of things it's the same person so who cares. I've worn odd shoes now for the last 2 years, it's provoked many great conversations about what is/isn't acceptable and I'm still unsure if the average person is right, I take pride in my appearance being wrong.
The "do 0 with his life and not speak to anyone" honestly sounds fine. Some just aren't all that aspirational, the place they live in is ok, the stuff they have is ok, what more do they really need? Whenever I've openly talked like this it really riles up some people as ok is apparently not ok.
If with the 6 month gap everything was fine after maybe just figure out when/how to distance more. It seems a weird thing to do but if both of you are happy with it then nothing wrong with meeting less or with gaps. I've got some friends I decide to only see once a month or so rather than weekly/daily as it just wouldn't be a good idea.
edit - when I typed this it was at the Moss reply