The home is in White Center and we are hoping for continued appreciation, however being able to supplement our mortgage with rental income is our first objective.

That's a good way to supplement your income and begin investing right away. 

Right now social media and sites like BP have taken over promulgated the message that real estate investing is good.. its a way to make money its a way to supplement your retirement and for some a way to quit their dreaded 8 to 5 and become a self employed real estate investor. 

You will make more as a contractor with minimal risk , I agree, @Matthew Paul - this is a great way to supplement income and diversify.

We supplement with 1-2 weekend per month in the off season.

Freddie is problematic for me because I need a supplemental loan to cash out the value add.

I'm 57 and want to supplement my income and eventually replace it with real estae investing.

Also, in regards to CBIZ, it is definitely something you'll want to look at as a secondary/supplemental coverage.  

In the event you feel like taking off a week or two without other supplemental income your finances may be squeezed.I'm in a similar boat and am becoming an agent to act as my side hustle.

I love what I do, but the plan is to supplement my income with real estate so that I can enjoy both the career and lifestyle that I desire.Keep it up!