Old WordPress sites
A theme or plugin that hasn't seen an update in years breaks on a newer PHP, so the site stays pinned to an old one. Now that old PHP is the problem.
What I do
An exposure check: which PHP version each site really runs, what breaks when it moves to a supported one, and what fixing each piece costs. Then we fix it: update, swap or retire whatever is holding the site back.
The exposure check typically takes about three hours a site, at $100 an hour