I am based in Europe, so it makes sense for me to follow this.

Brokered a client this 5br 2ba house in Portage Park neighborhood of Chicago but the cheaper less nice side of town for $350,000.

Using a VA loan for a second property, where I’d move in and rent out my current home.When I made an offer on a fixer-upper (I didn’t win that bid), the loan officer mentioned it might be difficult to convince the underwriter why I’d need another VA loan for a second property in the same area, especially since the new home is almost identical to my current one (same size, age, school district, etc.).

Exclusive and Regular Use: The space must be used exclusively and regularly for business.2.

I’ve used it for projects and think it’s great for high ticket sales coaching and information based products. 

This is a huge red flag. 

The plan is to complete construction in the next 1-2 years and rent them out on airbnb What made you interested in investing in this type of deal?

Does anyone have experience purchasing a mixed-use property on an auction site sold "as is" with a quitclaim deed?

This is not an exact science.

Please see  background on deal below, as this will be my firdt purchase.