I'd expect to read a lot. The best part of these trucks is how well they are documented. The TM's are FULL of detail, and while a bit misleading sometimes, tell you exactly how to turn a screw and how to troubleshoot a malfunctioning electrical component. I am an IT guy, not a motor pool mechanic, and I have changed tires, troubleshot CTIS, air systems, and engine issues like a pro (well maybe a bit slower).
Prepare girlfriend for no more dates. All money will probably be spent on the MV. Some lucky few have their significant other work on it with them. Hold onto that one.
You say you have to convince Dad, trick him into buying one as well, then it's a family hobby.
Daily driver? Better be a good, quick mechanic, and have a good parts place and access to spares. The PM for these trucks are not insignificant, have the time, patience and dedication to do it right. PM's are not cheap. Oils changes are not a $20 Grease Monkey effort. They are quick, but I'd figure $100 for an oil change. And that's just the oil change, recommended I think every 3 months if you follow the TM's, flushing the coolant, changing fuel filters, etc. I think some people find a good balance of the use of their MV's and the PM's, but a maintained truck is going to be more reliable. They are 25+ year old trucks, and will have some issues, be ready for it. I think anyone who has changed the steering knuckle will advise this is not a quick fix they could have done to their daily driver. Nothing more satisfying that fixing something yourself on this machine. Just swapping out a spare is an exhausting but fulfilling journey. Registrations, insurance, fuel, and parts (even fun upgrades) could easily spiral beyond your budget. Even the tools to work on the truck are different, and while you can get a lot from Craigslist or Harbor Freight, they all add up.
Psyched to see younger folks getting into the hobby. Read a bunch, go see one, volunteer on a recovery, go help another member with an oil change or a part fix, and try it imagine how you would have dealt with it financially and the down time you would have incurred trying to get to your job.
Go for it though. They are more fun than it seems and as long as you maintain it, you could sell it for similar money. Advice? I'd stick with a 2 door speck for the daily driver and have the beast for weekend excursions if you could swing it.