If you have had pneumonia a couple of times already in your life, are you more likely to need to be hospitalized if you get covid-19?

Not necessarily: If you were hospitalized previously for pneumonia then yes you would be at higher risk . The diagnosis covers a range of illness. The term "walking pneumonia" has been used in patients who may or may not have a true pneumonia, don't seem sick enough to warrant hospitalization or even an x-ray, but may benefit from antibiotics. We all experience such respiratory infections over our lifetime.