Every family is different, I guess. We take big ticket items and attach them to holidays:
"Honey what do you want for Mothers day?"
"Well I'd like that patio set I've been dreaming of, can we afford it?
"How much does a patio set cost?"
"I have no idea, a good one is probably not cheap."
"Well we we just got our tax refund. Let's go look"
"OK here is one I like can we afford it?"
"Probably will have to do the roof next year."
"Can the roof wait one more year?"
"Umm.... I think so?" (crosses fingers)
In the division of labor in our house I'm the financial guy, tasked with answering the question "can we afford it?" It's my job to say yes for a least a few items that aren't about skiing.
Part of our issue is that we deferred all home maintenance through the recession. Now we are trying to catch up.
"You just need to go at that shit wide open, hang on, and own it." —Camp