I live in Orlando and I am having difficulties finding a quad for less than $665,000 that will produce 1% or more in rental income. 

As a parent, your job is to produce good, competent adult people.

Knowing nothing else about you, I would suggest that you either find a way to make more money at your current job by increasing your production to fit your excess time, or make a jump into an RE field that will take 100% of your capacity.

$150K is at the upper end of the price spectrum for a rental property and may not produce the COC return that you want.

I think it depends on how big your org is, how many units will be managed, etc.I looked at a number of solutions and I had the added wrinkle of needing a product that was Canadian friendly (we are a bit unique here ;) ).

You are absolutely right about knowing your product. 

Vacation rental products: Some banks are buying into the short term vacation rental action so long as the prospective property is miles away from your home of residence.

Now, I need about $50k in repairs to get it back to livable again and I haven't been able to find a mortgage product anywhere with this credit score and a property that anyone driving up will see is damaged.  

Currently working full time as a product development engineer.

We currently still own it and it is our best-producing property.