Specifically I'm looking for information on the pros and cons of the loan modification process.  

I have played around with a few loan modifications and charged up front.

You should be able to come up with a template of sorts that can be applied to all your properties with slight modifications based on the property itself.

The owner has begun a loan modification with Wells Fargo.

I have to get permits if the project is going to result in making an any structural modifications, framing/plumbing/electric, but you can DIY it if you want.

He wants to attempt it again but I want him to understand that with his credit all jacked up the banks are not really working in his favor.The guy wants to use the owner finance as the last option and wants to rent it out now until he knows if the loan modification will go through, I think he is gambling on the wrong thing and will end up losing the house, leaving him nothing but a loss.  

Some items I look for are evidence of smoking, evidence of unauthorized pets, evidence of unauthorized occupants, evidence of pests, changes to locks, changes to electrical, changes to plumbing, unauthorized structural changes or modifications, maintaining proper egress to window and door exits, not blocking ventilation and HVAC systems, maintaining a basic standard of cleanliness, proper trash disposal, etc.  

I just got done with a drain modification required by the state on an existing pool this week.

I have a bankruptcy on my credit from 2008 and I just went through a loan modification 2 months ago, but I want to start investing in condos for rentals

You can try a modification,  deed in lieu,  short sale,  or maybe something a bit more creative.