I am based in Virginia and licensing requirements here seem manageable.

We run into this especially at out parcels in grocery anchored centers, and our users generally can't make a ground lease work for the business case so the next best thing does tend to be the BTS or we often do Reverse BTS deals where the majority of the building design and management etc is done by the tenant. 

I have a few rentals with section 8, and they are professionally managed.

If the negative cash flow is manageable and the appreciation potential is strong, it could be a smart move.On the other hand, investing out of state allows you to enter more affordable markets with strong, steady returns, helping you to build a diverse portfolio over time.

I currently manage a long term rental and working on a single family home fixer (will probably convert to rental in the future) in Cali.

As someone who occasionally works with these investors, I always try to emphasize the challenges that come with real estate like managing renovations, dealing with tenants, and navigating market fluctuations.

I follow the letter of the law( no matter how much I may not like it) that's part of my risk management and my reputation.

Practical Tips for Managing PropertiesFinding Good Tenants: Screen thoroughly.

It also includes managing your existing investment well to ensure you aren't bleeding money due to bad tenants, excess maintenance, etc. 

Managing a rental (even if it cash flows) comes with responsibilities, and it might not be worth it for $300 a month.