His wife doesnt work, but i think when getting the alcohol under control she has the ability to step up.Does anyone here have links i can show him that have simple breakdowns and arguments to why he should buy (and buy right) vs rent.

You could spend a few hours in one of those areas getting great food and drinks and walking around sucking in all the glory that is Chicago. 

I think I'll have a stiff drink, chalk this up to a learning experience and start looking for the next potential candidate.

I thought we just hang out shingle out and we all get rich and spend out days drinking umbrella drinks while the rest of the fools sit in their cube working for the Man...

Should I stick to enforcing that rule with no exceptions, eat the cost ourselves since he's a good paying tenants with little problems (besides his drinking), or find a halfway point?

Higher end clients drink more wine.  

If you are up for it lets grab coffee or a drink sometime.

You can't really blame some of these newbie wholesalers as they are drinking the koolaid tainted by these so called gurus that promises them the world but in reality they're only getting a grain of sand.The promises of doing this in only 5 hours a week with little or no money to make a ton of money is a luring and an attractive diamond being sold to the poor souls that buys into their game but in reality they're only getting a lump of coal.

He had a severe drinking problem and would just sit in his chair and soil himself.  

I would not absolutely disqualify it based on that, but I would certainly have to be talked into it....several times....likely with alcohol involved.