They truly are a good local business who values their employees and customers so I want to go with them for the leaks repair, and the annual maintenance. 

So Big-Gov. takes MORE from Walmart, which is YOUR $ that you are paying Walmart, for Big-Gov. to hire MORE gov. to then take $ for this slush fund, that gov. employee, and than sends 30 cents of that dollar and sends it back to you in form of some "benefit". 

I have contractor who will do all the work for me. 2- I am currently a FT employee with real estate investment as my side hassle ( 2 OOS fix and flip going on) .

In most states, the company that owns the property can hire an employee to manage the property for them without a license.

Here is my situation:- I'm a W2 employee that earns north of $500k a year- My wife is a stay-at-home-spouse- I'm looking to buy ~ $1,000,000 in STR Real Estate by the end of the year (as an investment and to offset my tax bill)I'm fairly well versed in the rules surrounding using STR to offset active income.

When have you ever had a interaction with a government employee and thought to yourself, "wow, that was a great experience."

The downside was he later hired employees which caused insurance and other issues running a business from a residential district. 

Job situation currently:Quick background, running an IT business for 3 years now, makes about 150-250k gross per year, struggle to find the right employee to help so it takes my time m-f 8-5. 

So, I would either work this through your brokerage if they do property management, OR you could become a W2 employee for the current building owners to manage their property without it impacting your license.

Also you can save a lot of money if pm has their own handyman employees and do not need to sub out all repairs. my experience is that STRs outperform LTR by enough to cover the PM fees, utilities, and additional furnishing costs but not much more.