My skin is crawling.

Then you have to be ready to deal with a multiple offer situation, which is more of a question of how certain you are of your numbers than anything else.

Being a landlord mean being thick skinned, being able to be objective, and to some degree having to be 'the bad guy" sometimes - not everyone is comfortable taking on these roles - best of luck to you - I'm looking forward to seeing how all of this turns out. 

There are more than a few ways to skin a cat, but to some extent the market will tell you what the optimal strategy is, if you just know how to listen.

I'm slightly confused thou because highest and best is usual meaning there are multiple offers but you are also saying you got a counter?

Also larger brokerages with multiple offices will likely have many seasoned Brokers willing to have you help out.

(Some of the books that helped me the most I have read multiple times) Financing your deals is not impossible if you have downpayment money, but if you have a BK and no cash, you're right, it's very challenging. 

If you have budget for multiple properties, and bandwidth for multiple markets, consider evaluating "deals" from both markets.    

I say ok, I think I can come up with say 10K to get "skin in the game" which should cover the 4 points easily on the type of deal I am looking at.

This is considered a hard inquiry because the renter had no direct involvement in the request.Many renters apply to multiple rental listings with different landlords.