My underlying question is:  How can I take full advantage of moving to an expensive market while utilizing a VA loan given my current situation, keeping my wife's loan-qualifying ability in mind if necessary?  

Let them know the area you are looking and get pre-qualified with a lender so when they bring you a property you can show ability to close.  

My take away is your ability to secure local financing with a bank that has taken a liking to you and your business model.. one cannot stress enough that simply shopping for lowest rates is short sided thinking when trying to acquire banking relationships.. its as much about a relationship as the pricing and the relationship is far more important than pricing..

Today, we are experiencing considerably more financing requirements than the past, and lenders are learning to actually use metrics to gage a person's ability to service debt and the underlying collateral, rather than simply originate, recycling the loan, then walk away. 100% financing to individuals w/ 600 FICOs is laughable these days, but was a reality in the past.

You are at more risk of issues with this tenant for imposing a late fee when the ability to do so is unclear. 

Higher rates tend to affect impact people's ability to service debt and therefore pay high prices for housing.

Your ability to "reload" for the next investment will largely be dictate by W2 and lifestyle.  

specifically we have a 6 unit that has water and sewer as the largest expense (and increasing significantly) so our thought was instead of increasing rent we would begin a bill back.  

If you don't have the cash or the ability to get a traditional loan, you may have to use creative financing or partnerships.

@Kenneth Garrett - One of the beauties of rental properties is the ability to generate PASSIVE income.