Cheating: I get it now!

My pandemic project has been starting a company. I love walking tours, and I thought I could create DC tours based on presidential history. I thought it would be cool -- and that it would motivate me -- to set this up as an actual legit business. At the start, I'd have no employees and I wouldn't need a physical office. It's streamlined and easy, right?

The good times so far:

I have paid $847.50 to the District of Columbia, and I am not yet legally allowed to operate.

• $220 in fall 2020 to register my new business as an LLC with the District of Columbia.
• $55 to register a trade name.
• $50 to get a certified copy of my trade name registration, to register with the DC tax office. (Not needed, but more on that below).
• $150 for a tour guide license. There is no certification process; you just have to pay this fee every year if you want to be a tour guide in DC.
• $300 in winter 2021 to file my LLC's "biennial report" -- which just confirmed that there have been no structural changes to my business since the fall.
• $72.60 for a Home Occupancy Permit. My business needs to have some kind of address, and though "home occupancy" in this case means me using my computer desk, I still need a permit to do that for my business. (This still hasn't been issued.)
• There's still the matter of a basic business license, which will be at least another $70. But I can't pay that until the home occupancy permit comes through.

And how about general confusion? So far I have had to create accounts with four separate web portals: for the Office of Tax and Revenue; for "CorpOnline" (a portal for registering corporations and LLCs with the city); for the city's Department of Consumer and Regulatory Affairs; and for the "DC Business Center" (which seems to be a separate portal for applying for a Basic Business License).

None of these portals are particularly transparent or user friendly, and from what I can tell, none of these portals talk to each other. But you often need documents and reports from each one to complete steps in another. And a few of these systems, despite having my contact information, haven't pushed out e-mail notifcations when important documents were available or more information was required. I've lost a lot of days waiting for information that the city didn't tell me was available.

This has been ... educational. I can afford the nonsensical fees, and I can sort of navigate the very confusing and poorly written web resources offered by the city.

But how many people can't? Maybe all this stuff made sense at one point. But if you're a small operator, or you're just trying to get ahead, there's a significant incentive to operate illegally.