I don't think it has anything to do with whether he thinks he's a good pilot or not.
The fact is, if a company is taking on pilots who pay to fly for them, once that pilot has done their stint, got their rating, or whatever was agreed to, they will drop them and take on the next customer.
If you are paying to fly for a company, you are a customer, not an employee.
Some hiring companies will recognize that you were a customer, and not an employee and therefore discount the hours you accumulated. Some will not.
But the point is, you are not guaranteed a job after having paid an outrageous amount of money to travel around to places you don't really want to go, and get a rating that won't be worth much, becuase if it's not current, and you don't have several thousand hours, in todays market, you won't be able to just move to the next company as an EMPLOYEE.
Think about it folks, if a company pays their F/O USD 20,000 per year, and then decides to take on "customers" who will pay USD 20,000 to be a F/O, they immediately turn a profit of USD 40 K. And if they were to hire you at the end of the year, they'd all of a sudden show a loss of USD 40 K.
Multiply that by several hundred F/Os and it's millions of dollars a year.
There's no way a company that has you pay to fly will hire you.
So before you do that, you have to make sure there's a market for people with a rating and 800 hours more than you have right now - that's because in a year you'll build about 800 hours.
so if you've got 250 hours, and the minimums at the regional are 1500 hours, you're not going to have the minimums after having paid to fly, so you'll STILL be out of work at the end of the year, and by the time you get the 1500 hours, your rating will not be current, so it will be close to useless.
You need to do like people have had to do for centuries in every job there's ever been (with some minor exceptions, this IS the rule). You start at the bottom, and work your way up.
In an office, you start "in the mailroom", in flying you start as a CFI, or short ferry flights, or banner towing, or skydiving, or patrolling.