Although I also think it's worth examining your mindset: instead of an action giving you a result you weren't hoping for being classed a "waste of time", just think of it as an intelligent way to make sure your operating at optimal efficiency.

For example, if we added a 4th partner who is based in Atlanta to live in the property for a certain period of time, could the loan be viewed as a regular way mortgage versus an investment mortgage, resulting is us having to put down much less than 20%?

The definition depends on a person’s point of view, but the end result is the same.

Generally speaking, would buy and hold investors consider a purchase of a portfolio of rental properties, 90% occupied, for 85% ARV if that 85% resulted in acceptable cashflow (say $15,000/month) and over $2 million in equity?

*Downside: This will be a upside down portfolio.Upside: possible can produce some good cash flow and it's no money out my pockets.

Now that my "nest" is almost empty, my focus has shifted to working toward making REI my primary income producer.

I myself am a Top producing Broker in Naperville.

The best results would be if you had a Contractor estimate you on the repairs.

I think that The Peak Producer program by Buffini is a good starting point for the beginning agent.  

A lot of information (and mis-information) I have gotten from lenders seems to be a result of their own rules and not actually loan guidelines.