Any recommendations on carriers who write aging commercial properties in WA state? 

.#2 and #3 don't have to be scary, as that can still be done using good debt, but the biggest red flag there is not knowing how to do that.

This just screams RED FLAG, STAY CLEAR. 

If you were going to buy it and move out immediately, that might raise a red flag. 

I pay $150/month for a four unit in my area (that was the best price from a reputable carrier). 

Additionally I know that I have to tell the VA that I am intending to rent this property when I move, will that send up any red flags to them with me having owned it for such a short time?

I'm reading the documents and they've flagged some environmental issues.

I'm going to talk to my lawyer to see if the property  can be flagged.  

The last thing I want to do is go in on a "good looking" deal that local folks here on BP could easily point out red flags in.

@John Sherron Lots of posts on this subject, but the main red flag is don't pay any upfront fees.