Here's what I think. I'm not much of a DIY person, but because I really want this vehicle, and have some sort of love for it, I would hope that my dad and I can do whatever needs to be done with it. I don't know much about cars, but he used to be a mechanic so he knows pretty much everything there is to know.
It'd be good for him to teach me the ins and outs of fixing a vehicle. Great to spend some quality time together.
If you really want that particular vehicle and your Dad used to be a mechanic, then the standard maintenance should be a breeze! And you have the right mindset that, if you really want it that you'd put more love and attention into it than just any other car.
And yes, learning from a trained mechanic is the best way to start DIY's. By the time you're looking to get into your 2nd car, you'll be knowledgable enough to do certain DIY's, while learning the intricacies of the new car that would be different.
Here's a good analogy. There are many in the world that are just barely purchasing their first smartphone (not just Android, but any of the current smartphone OS's). For those that pick Android as their first smartphone, they come to where they feel they'll get the most intricate advice that they may not get elsewhere, and we've seen/met many new Android Forum members, due to this being their forum of choice...but, once they've gotten a taste of Android and truly get some valuable advice about learning the OS, it's really up to their own merit of really allowing Android to enhance their experience, rather than not taking advantage of all the OS has to offer. So, by the time they are ready to upgrade, if they've picked up on Android quite well and love the experience, then they can take their Android Experience to another level with their next phone, while still knowing that they might select a phone that has a slightly different UI, than what they experienced with their first phone. If they didn't quite take to their Android experience that well, they can opt to go with an iPhone/Windows Phone or maybe even take a step back to Blackberry, but the basics/foundation of using a smartphone will already be there for them.
In essence, your 1st car experience and learning will all be up to how much you are willing to put into it. From the sounds of it, you're already on the way to a great start. I only wish my father knew anything about cars, so that I could work on my first car by myself. Lucky for me, my Uncles were all experienced with car maintenance, as well as some older cousins, so I wasn't short of resources, but if my father were as much of an enthusiast as I became...would've made for some fun times working on the car on Sunday afternoons. After 21 years of being a true car enthusiast, since I turned 16, I can't say that I got to the point of being a "mechanic," or ever being able to be a mechanic at any point, but I've learned enough that I'm able to join in car speak conversations, without saying anything ignorant and actually comprehend some technicalities that I never would have before, had it not been a hobby that I'd always wanted to have in my pocket.
One caveat, once you do get to making more money, be very careful not to let the "mod" bug hit you too heavily. I know it hit me hard, once I finished college and landed an amazing career. Modding cars can be extremely fun, but at the same time, take a huge hit to your wallet!
Enjoy!