HiCustomer what a situation! To begin, please know that the best advice I could give is the kind I would take myself.
I encourage you to say something along the lines of, "I'm going to a movie on Friday; I'd love for you to join me. You're such a cool guy." He will most likely accept, as he likes you. Continue to establish trust and rapport with him by being the one to initiate plans if you have to. Furthermore, help him with things. This could be offering an ear when he has a problem, taking an interest in the things he likes, or doing any other kind of kind deed. If he accepts on a regular basis and it is apparent that he enjoy your company, he will open up to you in time. By taking these steps, you two will begin with a solid friendship and possibly even more. I hope my answer has helped you. If you feel that it has, please kindly accept my answer. Good luck.
Do you think he would react positively if I tried to talk to him openly about the situation?
I've tried all these things in about a year and he is still having a hard time
at this point I feel I need to lay the cards on the table and make things clear or move on
Given these circumstances, yes, you must speak openly about it. It's unusual for him to have difficult with intimacy due to his shyness, but tell him your true feelings and ask him about his.