*"I have a friend who has been riding since 2012. Since that time he has crashed at least 4 times (that I know of, could be more that he hasn't told me about). I am concerned for him."
Difficult one, well you must know how many miles he has ridden and the type of bike? So rather than just say enough is enough I'd look for the root cause of the issue.
Experience- Each year most people ride the bike during summer put it away for 6 months and then drag the bike back out and believe that they can ride at the start of the season exactly the way they rode at the end of the previous season; they do not recognise that they have had six months of deterioration.
Type of bike - Some bikes are so focussed that anyone but a seasoned rider would have real issues. So look for a more forgiving machine.
So why not try to look at exactly what is going wrong ie overconfidence, lack of awareness and then book both of you on the course?
If all else fails then you may well need to have the conversation you clearly dread but I tend not to think that way, until a physical /mental issue leads me to that conclusion.
As I said difficult one but stay by his side
generally when it comes to anything with motorcycles it is a small community, try and get people to spread the word, example stuff for free? make videos? Market it i suppose, what would make someone go to your store instead of the one next door or why not go online...
Legal and insurance
I assume you are licensed to ride ?
MCN site & MCN forum feedback
5 months! I have never understood why men are so patient about these things. A woman would have had moved into the shop and refused to leave without someone getting things done.
Buy a Triumph instead. you can go direct to their customer service at head office if you can't solve a problem with a dealer and they'll get things done without a fuss.