It takes time and knowledge.

As I’m saving up for my first investment, I would like to learn more about the industry - and it would be nice to earn some income while doing so.Are there any specific skills or knowledge I need to secure a VA side gig? 

While podcasts, books, seminars, and websites offer general knowledge, you'll buy a specific property in a specific location, subject to local rules and regulations.

It could be a nice opportunity however I would be certain they will want you to make up the difference between $250,000 and whatever is left on the mortgage which btw in my opinion should be done with lender's knowledge and approval. 

Purchasing a “distressed” property and “repositioning” it requires significant capital for improvements, build outs, holding costs, maintenance.In looking for that “needle in a haystack” slam dunk great deal you’re competing with very knowledgable, greatly experienced investors with the cash to make no contingency offers and close in a few days.  

As important as due diligence, analysis, knowledge of the property type, track record of the syndicator, correctly predicting economic trends, and timing is, the number 1 way to avoid a devastating loss is NEVER INVEST MORE THAN 10% OF YOUR INVESTABLE ASSETS IN ANY ONE DEAL.  

I dont see this as a target rich environment for the NO money assign contract wholesalers.

Right now evaluating potential markets, I'd like to find one to focus on for my first 3 properties (building knowledge in a specific market). 

The real estate agents who are knowledgeable and doing a lot of deals each month will be the ones who can get you these accurate numbers.

And over 20 years, my partner & I have wholesaled or assigned quite a few deals.