It depends what you mean by "receiving a lot of money" and "substantially increasing" the bet. The place bet on 6 or 8 wins $7 for every $6 wagered. Let's say he started with a $12 bet and pressed $12 each time. That would go like this:
<ul type="square">[*]First win is $14. $2 taken into cash, $12 used to press, new bet amount is $24.
[*]Second win is $28. $16 taken into cash, $12 used to press, new bet amount is $36.
[*]Third win is $42. $30 taken into cash, $12 used to press, new bet amount is $48.
[*]Etc.[/list]
If he did this seven times, as you say, he certainly would have been taking a lot back and pressing substantially.
As for "comfort" with a place betting pressing system, it's important to remember that these bets are -EV regardless of what system you use. I would note that the lowest edge is on 6 and 8, then 5 and 9. So, if you press your bets more the farther inside they are, your blended house edge will be less.
I don't use a pressing system, but if you think one would make the experience more enjoyable for you, certainly go ahead.