My first and second times had pain involved, but I had great ABA support from the get-go to deal with DS' tongue tie and DD giving me nipple thrush. Being able to talk to someone about having pain meant I had a cheer squad and beautiful people checking in on our progress.
Support is one thing and is great, technical advice from a IBCLC lactation consultant is worth its weight in gold - for around $100 for the first visit it's value for money, considering how much formula (and associated expenses) would cost over a 12 month period. If you can nail it early you're kicking goals in so many ways. But I'm lazy, and that line of reasoning has helped me help other lazy mums in the past