I have been involved with self directed accounts in a number of ways.

The situations where land and/or vacant buildings were owned prior to 2018 are usually the most complicated and typically involve the a little more tax risk application of the OZ rules.

It sounds from your description that it is.However, because you also do personal activities in the room (play games on your desktop), it doesn't sound like this would pass the "exclusive use" rule.Playing the games on your laptop in a different room would likely qualify the room as "exclusive use" as a home office.Also note that in the future if you take this deduction, there is a simplified method you can use to reduce the records you have to keep - just multiply the square footage of the office by $5 (if it is under 300 total square feet).

I would proceed very cautiously when zoning is involved. 

I deal with the monstrosity known as the NYC building of department as well as smaller municipalities like in my hometown of Yonkers and there is a wide variation on the time involved and what they require.

Multiple subcontractors would be involved. 

Sometimes it gets people off their bark-a-lounger and involved but many times people spend the money only to find out they need one on one help through a couple of transactions to have the knowledge and confidence to actually be successful.

DM and we can meet up for a drink around Logan Square

They are open to the flexibility of the deal instead of trying to squeeze a square peg into a round hole of an exit strategy. 

LolI’m looking to be more involved here on the forums to learn from people with more experience than I have.