Unlike a traditional loan I hear that the USDVA loan is basically designed like a VA Loan, but it's designed for Fixers.Also...If you're trying to build a portfolio up why not do an FHA203K Loan FIRST.

Granted, if you find a deal where you can purchase both sides of the duplex, you can get a traditional loan that will treat the purchase as one mortgage.

In my current state of learning everything I can about RE investing, I keep coming across the challenges of getting financing after 4-10 traditional mortgages.

The effort I'd have to put in the 2 properties just wasn't anything worth while compared to the 240k property. 

Yes, it can be harder to get funding without a traditional W-2 income.

Find out how much the city utilities and taxes are compared to property prices and rental prices (craigslist is useful for checking rental prices), and then see where you want to start investing with the best return on investment. 

Due to the specialization of the plumbing and electrical, etc, I will have an above average outlay in cash compare to office/retail space. 

These would be your 'traditional' wholesale deals.

This would give you a more standard metric to compare apples to apples. 

You have to use your best judgement on what it would be worth after checking out all of the recently solds you can find and comparing them to your subject property.