The interest payments in the first half of most mortgages get you close to the standard deduction. Only works for owners, but it's still a relatively common one.
Yes, if you pay a mortgage and property tax, you should probably itemize. And/or if you have a lot of medical expenses.
Or, if one has a corporation (for freelancing, a SAAS, whatever), maybe the corporation could donate the stuff instead? I'm not sure how charitable donations work for corps, but might be worth exploring.