Shoot, I'm so sorry. It really sucks to have someone supposedly like your stuff but constantly make you feel bad. : ( A block feature seems like such a basic, important feature to have on any social site. D:
Feel free to disregard, since I know you said you weren't lookin for advice... but I know I've had people make uncomfortable comments at me/my friends back when I did a journal comic, and when I told them "hey, I know you don't mean any harm, but this makes me uncomfortable, please don't say things like this," some of them actually did dial it back.
IF YOU WANTED TO -- you obv have no obligation -- but if you wanted to, you could use this as an opportunity to private message this person and say "hey, sorry for deleting your comment, but I thought it would be better to send you a private message -- those comments make me kind of uncomfortable, and that's why I'd been leaving them alone. I'm sure you don't mean any harm, but I wanted to let you know."
I can understand not wanting to deal with that, especially if you're not a confrontational person, but the benefit is that you wouldn't have to be on edge waiting to see what he does -- if he responded reasonably to that, then problem solved! If he responded unreasonably, you now have a very good excuse to delete his comments and not respond, since you made your feelings clear. Some people are very very bad at figuring out that their behaviour is inappropriate. : (
Like I said, feel free to disregard. ;o; I understand it's a stressful fine line to walk and you know the guy's demeanour better than I do -- but I thought I would share my experience in case it is helpful at all. ;A; Best of luck, and I hope you don't have to deal with much more of that rubbish. : ( <3