Wish I would have seen this thread sooner, but lots of good advice so far. I agree with all who commended your good character and generosity, Grady. While there is nothing at all wrong w/ helping a fellow man, it needs to be done carefully for positive effect.
I agree w/ insisting that he fully investigate any alcohol/substance issues as a first condition, and that can be presented in a palatable way. In other words, it is not his fault if he has an addict personality/is alcoholic, but it
is his responsibility to treat it. Such a pre-disposition is usually inherited, so therefore not a choice. Recovery is a choice, however, and can make the difference between a successful life and an absolutely miserable one. Not being an alcoholic yourself, (I assume), you may not be completely familiar w/ all of the implications and behavior.
As for why he has not been in contact over the years, I lean towards the explanation of shame. You are one of the most exemplary men that I have had the pleasure of knowing, even if it is only through the internet, and also someone who has been successful in life. This can cause self-concienceness among the un- or underemployed. I have felt this over the last year myself, rational or not, it is real.
I am definitely in the camp of protecting you from having your goodwill abused, but at the same time you have a lot to offer someone who is less equipped to handle life than you. He needs guidance more than anything else, more than $$ for sure, and you are an excellent person to give it. Sure, in a perfect world he would have gotten this guidance when he was a boy from his father who loved him, but it's not a perfect world, is it?
I do quite a bit of volunteer work w/ addicts, I will PM you my phone #s and offer any assistance that I can give. It would be an honor, I really admire you.