What questions do you recommend me asking to optimize my efforts once I get a potential prospect on the phone?

I've found it's actually more common to have decreased occupancy but increased total revenue with PriceLabs, the opposite of Airbnb Smart Pricing.With PriceLabs you still essentially set your own price, and unlike Airbnb Smart Pricing the goal isn't really to simplify things but rather to optimize - you set base price, min/max, any specific rules you want, date specific overrides, etc. 

Incredibly easy to use, phenomenal customer service/support, and they take a lot of the guesswork out of SEO optimization.

The 100+ properties are currently run by the owner's daughter who seems to be doing a good enough job to keep it afloat, but not good enough to optimize the portfolio.

I mean, B&H is great for bldg a long-term portfolio & is definitely tax advantaged but: 1) with B&H you run out of capital quicker; flips help you build more capital (despite the awful tax burden), 2) sometimes you come across a great cheap property with a potentially high ARV but not such a great post-rehab target rent, in which case flipping seems optimal

Basically you have a 3 unit property that can only have all 3 units producing optimal return for owners that plan to occupy.  

Avondale is street by street but for the most part is going to be C class (or worse).Similar to @Alex Bacon, i have optimism about the area improving over the coming years and have recently been thinking about picking up some multi's. 

I am looking for some references on a Real Estate CPA in the Delaware/MD/VA/DC Area to help me get on track for optimizing the benefits of running a STR. 

We definitely could have done better managing/optimizing/marketing which in today's market plays a HUGE role in how a property performs. 

Hi Caleb, you should be VERY involved with an accountant as they are capable of identifying areas  in your financials that could use improvement and work with you to keep your money going in and out optimal and clean.