Is eye strain really that bad?

NO. Eyestrain really won't damage your eyes but is rather a symptom of an underlying problem. For optimal comfort and productivity, be sure to get a refraction for glasses to determine the true origin.
Not really. If you take breaks every half hour to look at something far away out the window, your eyes will have time to relax a bit and alleviate eye strain...Artficial tears such as systane may also help...