Healthcare costs are notoriously difficult to pin down and plan ahead. But to help you make estimates about your expenses, and particularly if you would be better off with a higher deductible plan, there are at least a few tools out there to help.
To estimate Medical and Dental expenses: https://www.fairhealthconsumer.org/
To estimate Prescription Drug prices: www.goodrx.com
It's also important to remember that Medicare doesn't cover dental expenses. If you do enroll in a Health Savings Account, remember to include savings now for future dental expenses.