Being in a postdoc that can last more than one year, I've not spent much time on job applications. I've just applied to two, so far.
One job I got via email and asked the person running the search if I should apply, and he said yes.
The other, the search committee chair actually emailed me to tell me about the job and said that he hoped I would apply. This job is particularly promising for a funny reason. I had a famous committee member Joel who had a female student Alberta whom I had heard lots of positive things about. I asked Joel to write a recommendation for me, and accidentally he made it non-confidential, so the dossier service actually let me read Joel's letter, which said that I reminded him of Alberta.
While writing the cover letter, I noticed that Alberta just started a new faculty position at this school! So what a great argument: this famous faculty member thinks I am like one of their current faculty members.
Though then I saw her picture, and I realized that it's possible that he was just saying we look alike.
Doing this particularly targeted job application process is surprisingly non-stressful. I worked with someone on the research proposals in my cover letter, the reason I procrastinate applications, and so far all I've had to do is insert a few additional sentences specific to the school. Now it's tempting to try others!