He had a serious problem with money, but he just couldn't bring himself to get into debt. At least he wanted to avoid borrowing money from his girlfriend at any cost.
休みにどこに行くかは、旅行にいくらまでなら出せるかをよく考えてから決めよう。
Before deciding where to go on vacation, I think I'll have to consider how much I can afford to pay for the trip.