I am hoping to slowly wear him down as the year goes. We're going in December. He was all, but we'll need a car on top of the airfare. I'm like, not if we UBER. No parking fees, and cheaper than a rental. I love going from IL to FL in 3 hours!
You don't need a rental unless you plan to go to a variety of places. (WDW+SW+USO+KSC) If it's Disney-only, Magical Express is free. They take you to your resort and literally put your luggage in your room. We stayed offsite many times when our kids were little (ahem, we were younger too) and now the thought of cramming bags into the trunk, and dealing with the rental car feel more like work. We still do it when we have to, such as our trip out west, but really Disney has us spoiled.
I used to use the SWA credit card to earn pts and we'd fly free quite often, or at least some of us fly free, or maybe just free one way, and pay for return only. Then I found the Chase Sapphire Preferred card and even though it's a little higher annual fee, I find the benefits well worth it. Chase Ultimate Rewards pts can be used to book flights, hotels, rental cars or just transfer them to one of several airlines and book direct with the airline using their pts/miles.
It's very versatile. Also spending on ANY travel (hotel, taxi, airport parking, rental car, etc.) or dining earns double pts whereas the SWA card only earns double for SWA purchases. Since a lot of our flights were free, it dawned on me that we'd rarely earn double pts for our everyday purchases when we had the SWA card. With the CSP, if we get pizza Friday night, it earns double pts.
When flights are free or half price, it would be easier to convince him.
Of course, if someone is reluctant to fly due to FoF, that's an entirely different story. No rationale will convince him/her. My BFF finally started flying again after dealing with FoF for over 30 years. They drove EVERYWHERE with their motorhome.