Your border runs won't affect your application. If you get denied, it will be because of insufficient money or that your chosen DTV activity doesn't require 5 years or access, according to the embassy you apply at.
I'm in several forums and haven't seen a single horror story of anyone being denied entry with a DTV.
But I keep seeing comments that there are "a lot of' horror stories out there. Where are they? Or is it the "The immigration officer asked why I was here, so I answered"-stuff that people are talking about?