A RE investor himself so he knows what to look out for and make recommendations to optimize your returns.

Pricing your property below market doesn't mean you are stupid, it means you will potentially bring in less money than might be possible under optimal conditions.

So the optimal income path from an investment perspective is, what sort of a job will get you into the highest possible pay early on for the least amount of education or certification or credentialing investment? 

The best and most optimal path forward will essentially be dictated by their wishes, and should take into consideration asset protection, income taxes and estate/gift taxes.

Some people do it the other way around, spending 20 minutes picking from the menu, then take the warm body that comes along as a tenant. 

While the market has been extra hot,  I think that's a bit of a nationwide issue and not just this market.Note that this needs to be very well managed with rate optimization dialed in tight. 

Can you offer any advice to optimize my financing situation and is there something I should be doing differently with my strategy? 

Many PM's will let you choose from a menu of services.

When an individual property is distressed and hits the market, it's not going to have those instant 12 offers and bid wars flaring up over them that you will see with those purdy perfect white picket fence Hollywood dream homes in areas with optimal school districts for their kids, etc. 

But generally speaking, comparable areas within 30 minutes of the city are on the menu.