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I evaluate the market every year especially now that limits are being placed on how much of an increase is allowed in certain areas. 

While you might lean towards long-term tenants for stability, short-term rental platforms like Airbnb can yield higher profits if the building allows it.When you get to Miami, I’d recommend visiting a few meetups hosted by South Florida REIA.

Forced appreciation allows me to build equity from the beginning of the investment, so if I need to firesale for an unforeseeable reason, I will not be underwater.- Debt-Paydown is a result of time.

I’ve considered mid and short term rentals, but from what I’ve seen, Baltimore city unfortunately does not allow new short term rentals unless the property is owner occupied. 

Then I did more research and found out the City of Inglewood does not allow you do STR with a newly built ADU.

If you have a multi, I usually recommend not allowing tenants to store items in the basement.

The quicker cash flow may allow you to scale quicker if that is what you want while the better appreciation could increase your net worth more over time.

And this does not include the real world issues, namely are you even allowed to convert this property to a four-unit and taking a single family to 4 unit is very likely going to cost more than $110k (but this depends on the actual layout and work scope).

Commissions are generally considered part of the acquisition costs, which are added to the property’s basis (the starting point for calculating depreciation and capital gains).Since you’re planning to rent out the ADU, you could depreciate the ADU's share of the property over time, which may indirectly allow you to benefit from the commission expense.