Anonymous participant Are you able to prove that you will have ongoing work or activities for 5 years? This could be considered evidence of being a legitimate DTV holder. We have seen applicants whose plans consisted only of a two-week cooking class and a single medical appointment in the past. More embassies are now stricter on these.
As mentioned, you'll need proper documentation to be a legitimate applicant. They will weigh the pros and cons of your application. Multiple stamps could be a red flag, but that's not the only factor they consider. Immigration may take a greater interest in it when you cross the border. Again, if you're legitimate and able to answer any potential questions, you're fine.