Otherwise I can't see the upgrades being worth the cost to you.

I require all prospective tenants to see the property first so they know exactly what they are getting.

If only one you may be able to add just another shingle layer to it for cheap.If there are a ton of shingle layers which usually shouldn't be more than two then you put undue stress on the structure and you might be in a county or city code violations for unsafe practices and conditions.The next thing you need to do it go to your attic space where you can see the under board of the roof and it's condition.

The tenant will pay off any loans on the property and you will see the monthly rent checks rise over the years.

Then, the third time they checked after the listing agent said it was accepted they see the water damage.

I'd be interested to see the numbers. 

Just look at the top of any marketplace post where you see the number of posts and you'll find it there.

After reading the conditions of my lease, it states that I have to cooperate in showing the property to potential buyers, or if I'm moving out to allow new potential renters to see the property.I understand that if it was my condo and I choose to sell it, the inconvenience is something that I sign up for as well as the ramifications. 

I told him he will need POF to see the prop.

I don't see the problem with you attempting to wholesale with you living there and knowing the sellers.