If you had posted this in the detail/wax section, you might have attracted the more OCD side of BITOG and received more recommendations to get the dents fixed via PDR. I sometimes comment about the evils of letting ones material possessions command your life (been there, done that, attempt to manage it). Some people spends thousands on vinyl wraps, bras, ceramic coatings, weekly washing, etc.. I attempt to practice moderation.
If your penchant runs towards uneasiness if everything in your life is not absolute perfect, then it might be good to relax ones standards on a 10 year old car. If you tend to practice moderation, then maybe getting the PDR done is the better choice. You indicate you wish to keep the car another 5 - 7 years. $300 over 5-7 years is not unreasonable, especially if you consider this as discretionary expenditures (i.e., give up Starbucks/eating out for a few months if needed). Heck, people spend hundreds golfing, at the gym, etc. for enjoyment. If having the dents repaired gives you satisfaction and enjoyment for the next 7 years, then do as you please and forget our opinions! It sounds like it is a decent car worth keeping up.
I hope this makes sense - my two views of the situation. I've had 3 pdr repairs on my 9 year old lowly Patriot and have zero regrets. I also spend $120 yearly for Krown rust proofing with no regrets (most rust free vehicle I've owned in 5 decades). It's our one and only vehicle.
