I would look at the ROE differences between what you can make now by selling, including the yield on that lump sum if reinvested in the current market conditions, versus what the property will be worth at a point in the future (5 years, 10 years, etc).

Am I passing up on potentially lucrative house hack deals because I'm taking too much out? 

Dump them and move on or keep losing 900 a month for the foreseeable future. 

Potentially using some creative financing.

I'm interested in networking, advice and potential partnerships.

This is the 2 units + 2 ADUs scenario.I am worried Scenario A might push future financing option into commercial real estate only, which will limit my cashout refi options and the future buyer pool.From a lending perspective, since a "Land Use Restriction" is required to be recorded on the Deed to limit rentals to be longer than 30 days, the property thus will not be considered a true "5 unit commercial property" and my worries in Scenario A will not come to pass, right?

I know it is too late at this point but should you find yourself in this position in the future I would utilize the 1031 exchange option.

Buy and Hold: Norfolk (Best Cashflow Potential), VB (Townhomes tend to work well, Green Run is a great area for cashflow), Chesapeake, Newport News, Suffolk (Less Military presence which is why i would put last.)STR: VB (in the proper zones if you have the money $850K+), Norfolk(Ocean View area specifically but have to watch out for the AICUZ restrictions), Leave the restPart of that decision process is distance to that I would need to travel to deal with rehabs, I hate dealing with the tunnels so I would almost always pick places on the peninsula last since I am based in Chesapeake.

I would love to connect with Multi family investors, developers, etc. to potentially collaborate with while building my network.

I followed a very similar approach as well and I must say that this method works not only for your first property, but for the future portfolio.