I was always concerned about someone seeing where I left my shoes and stealing them, thus stranding me far from home so I would ask different homeowners about leaving my shoes on their porches, hidden in their shrubs, etc. It became like a game to see how people who never met me before would react to this strange request. I did meet alot of nice people along my route though that remain friendly to this day! I think I also might be converting one of them to barefoot running.
Did you check the size of their feet before making your request? Possession is 9/10ths of the law, you know.
Good idea about leaving the shoes and running a loop - I'm occasionally taking my shoes off and running with them in my hand - don't know why I didn't think of this.