It seems like every city, county, and state has its own rules, permits, and tax requirements for short-term rentals, and I’m finding it overwhelming to navigate all the different layers of compliance.For example, some places require business licenses, transient occupancy tax permits, or even special zoning approvals.

(cash flow, tax benefits, potential for appreciation) Whats the timeline?  

There are a lot of LL advantages due to the low vacancy rate.

Great point about state income tax, @Jay Hinrichs.

Luckily both sites collect the taxes for our place.Our little town did implement a 1% tax that I have to pay separately.

We called them out on it and asked for tax returns.

This is because the dwindling cash flow due to the increased rates has resulted in higher cap rates.  

I’m told taxes and insurance is lot and will rise each year and cash flow is hard to come by.

Expenses: What are the operating expenses, including taxes, insurance, maintenance, and reserves?

The promise for the prospective agent to represent every flip from the buy side to the sell side is only as valid as the agent's due diligence and work ethic, and trust would need to be built in the process.