Lots of great buy and hold info here ( I have a blog posts on classics of lanldord lit  and all those books should be free at the library)..also, of most interest to you may be some of the strategies for low down payment on this site (some involve owner occupancy of a 2-4 unit, for example, or others involve more creative financing) to avoid the traditional higher downpayment for investment properties.

The house also sat unsold for a while, so he ended up reducing the price by $10,000 to about $98,000.Actually going through a traditional mortgage company was SO MUCH more off a hassle than I expected and there were so many issues I honestly don't think I want to list them all! 

Being raised in a traditional Filipino family, I knew right off the bat that my parents wouldn't be supportive at all of the idea.

@Jovan Hsu, traditionally residential is valued differently than commercial.

Those are all advantages you bring to the table that traditional buyers can't.

So, in a listed property transaction (Which this WAS NOT), you traditionally have a SELLER, represented by a SELLER’S AGENT, and a BUYER, represented by, you guessed it, BUYER”S AGENT.

I've read that traditional banks will offer around 4 mortgages, and then it gets much tougher, probably requiring new avenues such as portfolio lenders, but I wonder if we could even get those first 4 mortgages?

This means your buyer would only need to take out a traditional mortgage of $300K.Also, I believe (don't quote me) that in this scenario the buyer would be able to avoid paying PMI as the balance on the first lien would be less then 80% loan to value.  

We both have traditional incomes coming in. 

Depending on your market, you will likely get a higher price than if you do traditional wholesaling.