Investing in your home state or in another state with no income tax or a tax advantage can boost your post tax return significantly. 

The network and broker you are with can certainly help boost your success, but in my opinion nothing replaces putting in the time and being creative with how you operate your business to show how you, as an agent, are unique to your clients (Investors, people planning to buy for their primary residence, etc.)I also have an REI mentor who has helped with my process a lot if you would like a recommendation.

Though he has more experience with rehabbing this is not something you need to factor in to your answers as it isn't something that will influence or affect our agreement financially or at all.

The benefit to this was—I was able to purchase cheaply, and put more money towards some interesting renovations that boosted the home value, and made for some awesome perks for my future tenants. 

Can be a nice boost in cashflow in markets with higher electric rates and/or solar incentives.

So far I am only working with a few clients that I have found organically and haven't yet started aggressively reaching out to my sphere of influence or marketing for leads.

You can see in just a few years how the VA property can easily be a bigger boost to your net worth than the Memphis properties.Now realize that even with a PM the scaling of the number of units implies more work and effort.  3 units is unlikely not to be more work than 1 unit (assuming similar asset class - Class not lower than C+; I only recommend expert in slums try the D+ and below rental units).I would not choose the historically low appreciation markets but if I did it would only be for MF+.  100 units at $200/month cash flow can be significant even if the cash flow only increases at the rate of inflation; this likely provides a very nice life but probably not financial freedom especially if you are living in San Diego.  500 units with that cash flow most people would have financial freedom. 

If anyone is familiar with massachusetts, the areas vary widely- cape cod, new bedford, taunton, south shore, and of course boston itself (out of my league d/t price) are all much different in price/rent ratio, schools, crime, etc... what are the things that matter most to you and influence your decisions when looking into different markets?

That cost may influence your decision on what to do with the property.

@Hadar Orkibi, one trick to boost your credit score (sometimes significantly) assuming you pay your cards off every month any way as you claim, is to pay them off right before they report to the credit agencies.