You would not doubt stay involved for the comfort level your friend has with you but there are a wide variety of nuances with any commercial lease that would dictate the need for someone who specializes in the product type.

So eventually, a basic level of standard comp analysis will be required. 

So yes, your ongoing cash flow will be less once you borrow more, but, the reasons you'd be buying that second property are: it's undervalued; and/or it has potential for you to value-add using your specialist skills; and/or even when you refinance all your deposit back, it'll still be paid off by the tenants, with no further regular payments from you.

If you want to be analyzing that many deals (even when narrowed down to 10 MSAs you'll be looking at a lot of deals), I would stress that broker relationships will play a major role in your success level, in terms of finding good deals.

@Chad Linn I don't see us getting to those levels anytime soon, but I do think we'll see the next several years with 5%-7% perm rates.

What level of flip and what part of San Antonio are you looking at? 

If I had the property under contract, who would I approach at the government level and how would I approach them?

At your current level,  your rental income will not help you qualify for loans. 

I've developed my own system, that involves the following:1 - The 3 Pillars (mine) of REI...Market Analysis, How Money Works, and Developing a REI Plan...and how all three are equally important, and must work as one.2 - My REcapS System (a system within a system) that is a 3 Level circular (perfect) system where Level 1 feeds Level 2, which feeds Level 3, which comes back and feeds Level 1 again (thus the circle, or perfect system). 

Even after gaining my degree in business I still haven't forgot about my years working in construction and now I want to get back in and start building wealth with real estate by implementing the knowledge that I gained from construction as well as using the business skills that I have acquired from my job.