I think the problem that most people have with the manner that Steve has chosen to go about starting his business is that he hasn't paid the dues that most of us have had to pay to gain the applied learning that we have aquired.
When you buy a truck and then don't even understand how dangerous it is to bobtail if you don't understand stopping distance increases when you are bobtailing, it raises eyebrows of those that have already learned things such as that through experience yet have never thought about being an O/O because it's not their cup of tea.
The shifting problems, well, that could be an nuance of your particular truck or it could mean you just haven't got the "feel" of shifting that particular pattern yet.
While I don't pretend to try to speak for others, these are my observations. Are these hiccups a bad omen to your starting a successful career as an O/O? Probably not but it does cause others to reflect and wonder why not go about it in a more "proven" method, i.e.; become a company driver first to see if it's even for you.
BOL