One of the best things about real estate in my view is that you don't really need a lot of "technical" knowledge like other industries - you can just use your experience interacting with RE day to day to have a good foundation.  

Additionally, as the sole person running this business do I need to set it up for my properties to pay the PM company and then the company pays me as an employee or since I'm the owner of the company I don't have any employees and so there would technically be no employee side? 

You technically can not take debt to fund a downpayment of the property 

The reasons being, rent by room is technically a boarding home style of operation, think halfway house, elderly care facility, childrens home, etc. 

While some lenders can get creative with income and/or don't require personal income underwriting, DSCR lending programs technically only apply to SFR 1-4 units and small multifamily (usually to 10 units). 

I know this is all very anecdotal, but I'm sure there are a dozen places where you can find more technical information on neighborhoods. 

According to them there is technically no such thing as a “Do Not Mail List”.

Sorry to hear you got caught up in technicalities of the renewal.

Last time I looked the laws read In order to practice any kind of property management (applies to STR technically but is kinda gray area) in Alaska you need to be a licensed agent under a Broker unless you manage 4 or fewer units or if they are your personal units.

It is technically possible to 1031x into land that you already own and improve it.