My opinion is that this is really a personal choice and a factor of you and your wife's outlook on risk vs. opportunity. 

Much simpler and they can be screened by professionals without you lifting a finger.

I'm based out of Hampton Roads, specifically Virginia Beach and I'm looking to start attending some local REIA's and general networking with other investors, marketing professionals, Real Estate attorney, title companies, builders and contractors etc.

start with professional or nuce pics and a good listing. get vacation rental insurance and a reliable house cleaner and you're good to go. also make sure you line up back up cleaners in case they flake. also get coded door locks so guests can self check in yet not lose the key. is that what you meant?

I have been analyzing this deal to death and I feel as though I need a fresh outlook to provide suggestions.

With the limited info that you provided, I personally would keep it in my portfolio as long as the unit is cash flow positive and the outlook for the location and overall rental market is positive.  

Perhaps she needs some counseling and someone with professional experience to help her sort out her finances. 

I could have just gone to TREC but instead tried to get PROFESSIONAL advice. 

I don't know anything about the listing agent, but the listing broker is a long time local broker, second generation at the ReMax office his Dad started, and was very professional and rapid in his handling of it. 

Either way, you can hire a professional who can fight the tax increase (if egregious) on your behalf.