You are in a tough position. We live very far away from the Academy, and like everyone, time and money is always an issue. I agree with all above that having at least one family member present at each event is important. I Day is truly one of the most memorable experiences a parent will ever have. We have friends who opted not to go last year and sent their son alone. She says it was a regret she now carries because she does miss having the memories,. I think her son was fine, it was more that she wished she had gone.
I Day- It is such a stressful and busy time, but when our Mid showed up on T Court for his 30 minute visit with us before he was wisked away for Plebe summer, I was so happy that we had made the choice to go. Also, the Fly Over, Navy Band, Oath of Office, I get chocked up just thinking about it now.
PPW is a lot of fun because you get to see the success of your mid and they are so excited to show you their rooms, uniforms, what they have learned. My son was very locked on during PPW. We brought some extended family and that was a bit stressful as again, like I Day, family wants your mid's time and all they want to do is sleep, eat, sleep, and watch TV at that point. So, there you have it. Is it clear as mud?
ps- not sure where you live, but we actually found a flight that flew intp Reagan National in Washintgton DC that was cheaper than going into Baltimore and non stop, which allowed us to fly in and out quicker. With our rental car, we actually paid less and spent less time in the air and on the road. Explore the options on those travel websites. You might be surprised at the deals you can get. Lots of area hotels will also work with you on a discount for these events.