I realize it's a business and an investment, but has anybody had the awkward/unpleasant experience of kicking someone out before moving in??

That just seems like an awkward situation, to pay yourself out of someone else's account.  

Our current tenants are very nice but they don't leave for showings which makes it a little awkward.  

I find that it makes things too awkward.

A very small percentage of these folks actually reestablish contact and proceed with the application.Pros: (1) ABC "Always Be Closing" - ask for the "sale" at the closing on someone who seems solid; "A" tenants don't have a chance to get placed by someone else in the meantime or flake out when it comes to meet for the receipt of the deposit to hold(2) Streamlines the process IF the applicants check out (see below)Cons: (1) sketchy people have dressed nice and behaved long enough for me to accept their deposit (and then I am aghast when I start doing my screening) which finds me awkwardly returning the deposit on someone who was quite as good in reality as they claimed on paper(2) no time to do proper due diligence before accepting moneyI know some landlords take several apps (either all at one showing or in series over several showings within a day or two, then contact their "best choice" to offer the unit to them.My concern is there is a delicate dance that needs to be executed with great applicants, as they are looking for a place for the next month and can't sit idly waiting for a landlord to call them after reviewing their application.  

It makes people feel awkward.

Just create a spreadsheet to keep track of monthly expenses.For a roommate, asking them to insure their stuff might be awkward.  

That can actually be awkward from a tenant's perspective, too, though.  

If things go sour it will ruin your friendship and with acquaintances it makes the mutual friend(s) feel awkward.

It keeps you from those awkward conversations and from wasting time =money.