I have also used apartments.com (for some of my SFH), I prefer zillow. e-renter.com does a good job if you just want the background check and none of the other services.

What I would suggest alternatively is putting a clause in the lease that anyone above the age of 18 that's going to be living in the unit for more than 7 days has to be approved by the landlord and pass credit/background/income check etc. 

Would you suggest a newbie gets their license and buys in cash? 

If the higher insurance rates are a concern for you I suggest staying away from the high rises for now.We are surrounded by multiple military bases so there is always someone buying, selling or looking for rentals in our area and surrounding areas.

Given the demands of my day-to-day job, I would like to remain passive as much as possible.

I failed to mention he doesn't have a job, he is solely living off this lump sum which I thought was fine considering all the great references I received. 

Which loan would you suggest that will allow me to keep this a rental property from the beginning?

The rent would likely increase as new developments in the area add more expensive units but comps are all suggesting 1500 for a similar size updated SFH 

I suggest joining the Greater Orlando Real Estate Investor Association in Altamonte, you can meet a number of investors and wholesalers there.

Can you suggest the best places to go for someone who is new to this?