I haven't personally done this since I've stuck with SFRs, giving up some of the better cash flow and diversification from multi's in exchange of a better renter pool, appreciation, and liquidity of SFRs.... again, a great question for your mortgage broker/banker, though; this is why it helps to network and build your local REI team, as well as your virtual one here on BP ...

Does anyone have any advice about marketing in small counties or should I consider doing a virtual wholesaling business in a different market?

You could hire a virtual assistant to do that for you.

Ofcourse there's always the appeal of a virtually-guaranteed rent and a potential longer-term tenant.

I'm an animator, filmmaker, and photographer by trade, and I own investment property in Manhattan and Indiana, and have begun setting up a virtual wholesaling business in Austin, Texas. 

But I understand the appeal of the virtual option too.I would say, if your only goal is to access the MLS instead of listing houses for sale, then virtual is fine.

Has anyone tried to automate this with a virtual assistant on Upwork for example?

Just curious, to see if anyone using a virtual assistant.

I am connected to a vast resource of passive and high end private serious investors. 

Virtual assistant?