'Rich businessman' types can be a nightmare. I've had one. Definately not used to being criticised or told what to do. Mine tried to fit a ppl into an already hectic lifestyle and invariably cancelled with about 10 minutes notice or just plain didn't turn up. His motivation for flying seemed to be purely as a lifestyle accessory to be flashed around along with his Bentley. He couldn't be ar$ed with such tedium as preparation, study, planning, checks etc. There was no feedback from him in briefings other than the occasional bored/frustrated look at his watch every 2 minutes. The crunch came when we reached nav; he considered any planning or application of navigation technique to be pointless when he could just 'look out of the window to see where he was flying to', and continually asked to change the nav route to include flying past his mate's/bird's house.
How did I deal with things? A frank chat that if he wanted to progress towards a licence seriously then some application was required. If not, then he would be paying £100+ per hour for accompanied pleasure flights with no training progression or goal in sight. Never saw him again...
An instructor mate taught another 'rich bloke' to fly. The guy was utterly terrified of stalling, and offered my mate a considerably sum of money to skip the stalling exercises and continue onto circuits! Mate refused the money and told the guy it was correct syllabus or nothing.
The bottom line is that although these situations can be awkward, the first priority of a flying instructor is flight safety. Ultimately, if that means turning round to someone and saying 'sorry mate, you're really not cut out for this, I'd advise you to reconsider doing any further flying' then you're doing everyone a favour, most of all the student, in the long term. I've seen more than one PPL described as an accident waiting to happen who has eventually piled into a mountainside in cloud and died of deceleration sickness.
As far as younger students are concerned, bearing in mind that people can pitch-up at the age of 14 and begin powered flying training, I have had problems with some teenagers being too immature to accept constructive criticism. Some also have difficulty accepting the magnitude of the responsibility of being in control of an aeroplane(put simply, they don't fully appreciate that if they make a complete bollox of it it's 'goodnight vienna' and burning wreckage.) Having said that, I've seen some naturally gifted students solo at age 16 in complete confidence with an excellent mindset.
I recently did my taildragger conversion as a 2000 hrs+ instructor, and was taught by a guy who had only just passed his instructor course but had been in Tiger Moths all his life as a PPL. It was quite bizarre, in that I considered myself very much the raw student again, hoping that he could rescue the aeroplane if I cocked it up, while he sat in the back wondering if his instructional technique was up to scratch thinking that I was critiqueing him! (I was flying a Chipmunk on a tarmac runway in a crosswind). We survived, as did the aeroplane, and he did a good job. (I was determined not to be presumptious about how quickly I would pick it up, and, yes, it was still far more difficult than I thought it would be!).
Most experienced ppl/professional pilots I have done conversions or check trips with have been thoroughly professional in their attitude, particularly the multi-engine/multi-crew guys who have been away from Cessnas and Pipers for a while and have approached the task with a suitable amount of caution. Even the ex-Concorde man being checked-out in a C152 by a mate of mine who insisted the whole flight be done multi-crew! "Err, the gear's already down. It's bolted there..."
ST