I am now about to complete my third jet type rating, after some nine years airline flying. I paid for my own licence, and have no issues about that. Other than the light aircraft ratings required for licence issue, I have never paid for a type rating. However, I have to admit, I have been luckier than some. There were times when I was tempted...
As a return on investment, I am unlikely ever to entirely recoup the money I have spent, and the earnings lost (not only during my training, but also during my time as a Flying Instructor). However, this was a trade I considered worthwhile. I enjoy my life every bit as much as my friends who are accountants, despite their earning in some cases around six times my current salary.
As for the respect issue, I consider both pilots and ATCOs the equal of the highest levels of other professions. The difference in pay between us (pilots and ATCOs) is not that great (maybe I've been mixing with too many ATCO1s?) and is perhaps justified less by the money pilots have spent, than by the relative insecurity of our jobs. Whether the outside world considers us professionals or not, we have our own standards, and as a group we keep improving them.