Maybe time for a new platform to emerge out of this and Airbnb regulates themselves into retirement.  

How long does it usually take to find tenants for a new rental property especially your first, because the tenants will be the ones supplying the cash flow and the mortgage payment.

More than one person has said that to be successful, copy what other successful people do.Given that you are just starting out, I can't emphasize enough that you need to learn the real estate business (and it is a business) as well as the local market before you spend any money on buying property.I will (partly) answer one of your questions: Overall, Maryland is not, in general, a business friendly state, but each jurisdiction has its own rules and regulations.

I know there is regulations in regards to being dual licensed especially when it comes to FHA.

Location is critical.Even if the supply is greater than the demand, the good ones are full and the others are not.Some of the keys to success;1- Location, location, location.

Retail supply is a problem - so I think this is what is maintaining current pricing levels in Central FL anyway.Locally - investors are pulling back from new purchases. 

In Central FL - we have seen a drop in number of transactions - but believe it is due to shortage of supply (people don't want people in their homes). 

Silicon Valley championed the concept of turning America into a land of entrepreneurs taking advantage of flexible hours, unimpeded by regulations or specialized training.

book keeping, computers, office supplies, internet services, etc?

At the same time, the new regulations allow for the ability to put the money back into another pre-tax account like the SDIRA.