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.
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.