Originally Posted by Mikesumus Prime
Yes i know all of that already. My question is are there any other inns other than the ones in Ivarstead, Riftin, Windhelm, Falkreath, Solitude, and two in Whiterun?
Yes there are....http://www.uesp.net/wiki/Skyrim:Inns
It's pretty much random as to which one he will show up inside. It is not necessarily the first one after you reach level 14. Just keep visiting the Inns and he will show up sooner or later.