When the law was first implemented, VRBO was behind schedule and for the first month, I had to collect and remit the city & state occupancy taxes for my VRBO bookings.

My question is, when all these companies implement AI to replace all or almost all of their entire workforce....when they go to sell their products there won't be a market for it.

I think you've got to match your market to the strategy you want to implement.

Once you get approved start looking for townhomes, condo or even single family homes in the DMV area where you can purchase and implement an Short Term Rental (STR) strategy. 

Implementing the proper legal and financial structures can help shield your personal wealth, reduce your exposure to litigation, and limit access for potential creditors.

Purchasing single family then multi can be extremely tough but going from multi to single tends to be much easier.With this being said, this is just small part of implementing a successful house hacking strategy but plays a massive role.  

Improved lighting, technology, advertising, added a website, implemented tenant protection, and enforced rules/fees.

The key here is be sure you stay consistent with your implementation of this policy.  

If my best fiend told me they were going to implement this plan I would tell them not to.Dave Ramsey talks a lot about making a career switch from your W2 job to your self built career.

Factors which the commissioner may consider with regard to an application for a commissioner's adjustment include, by way of example and not limitation: (i) the relevant geography, (ii) the relevant population density, (iii) the degree to which the sought adjustment varies from the prevailing limitations, (iv) the size of the relevant building and the number of units contemplated for the proposed use, (v) the legal nature and history of the applicant, (vi) the measures the applicant proposes to implement to maintain quiet and security in conjunction with the use, (vii) any extraordinary economic hardship to the applicant, due to special circumstances, that would result from a denial, (viii) any police reports or other records of illegal activity or municipal code violations at the location, and (ix) whether the affected neighbors support or object to the proposed use.