There are so many people that just go online to register their pet, and there are many online websites that will provide a letter for this. 

Your county does not have a great website with all the online tools they should have, so you may need to do it OLD school and call them or go down there!

Are there things a newbie can do / provide that would be useful to those in a position to provide legitimate mentoring?

For the most case, for the stuff discussed on this website you don’t need a degree.

What would one recommend investing in a Major downtown, metropolitan area, like downtown LA or SD for generating positive cash flow?

if so, the focus on rent roll, your good credit, etc.According to what I saw on the VA website, you would be eligible for a VA loan for multifamily upto a fourplex if you lived in one of the units.Additionally, it is common for banks to consider the current rent rolls in the lending decision.

This will position yourself well so if the market does take a sharp decline you will be positioned to take advantage.  

You can't sell it to two different people...at the same time...and, you can't have what would amount to 2 first position leases at the same time.You can buy it on an option since the option has no lien rights...you're not buying it...yet. 

I finally found one where I've made an offer and the seller accepted (a few days ago) I just want to double check that you guys think this will have positive cash flow.

In reality, you're still not in too much of a worse position than you placed yourself in, because after all, it hasn't been coming out of your pocket (so far).The question remains: do you still have any equity left in the property?