I live in one and rent the other for positive cash flow of $400.After all is done, I would have 2 rental properties.

To my understanding the VA only cares that the initial person that purchased the property had the intent to live there and make the home their primary.

For those STR operators and investors that are not comfortable self managing (communication with tenants, scheduling cleaners and organizing supplies) one option is to hire a designated full/part time employee. 

I live in Iowa and I'm seeing nothing on the web for my state. 

I came across some websites that mention hypothetical health concerns about living near a gas station.

My plan is to live in it for 1-2 years while house hacking one of the bedrooms.

Like @Michael Bowman previously stated, I am completely comfortable paying a set fee to cover administrative costs as long as that fee is reasonable, established upfront and the PM is seeking to negotiate the best rate on my behalf. 

To win as a first-time or seasoned house hacker who is ok with less space, you want to look for funky layouts.For example, a three bed and a one bed is a huge score because you can live in the small unit and make more money without room hacking or wasting space in your unit.

But where I currently live (SF Bay Area) is so expensive.

There are things that need to be done that we simply can't do with them living there.