I think that's a pretty good way to look at things to determine if it's worth it to try to do the job yourself.
I've taken on a few projects and factored in "what if I totally screwed it up and have to do it over" and still came out ahead.
But some things you do simply for the enjoyment of it. I could easily hire out the lawn care at my house. But I like to do it, even though my time would be better spent working.
$750 to stain a deck seems like alot to me though. You can buy a pressure washer for $100 bucks, a few rollers and brushes for $25 and a few gallons of stain for $50.
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