Too big of cam?

All, very good advice and thank you for taking the time!
I'm new at engines but willing to learn. Although it is a dream to someday fly down the track, right now I just drive to school and back. I do want a quicker faster car, but I'm not going to be doing any racing any time soon. I would be happy with a good launch at the light when next to a ricer and then let him go ahead to get the ticket. (Just kidding if you're reading this Pops.) I also want to be able to drive down the freeway every now and then and keep up with traffic.
I totally understand and agree with making sure that the car is tuned before spending much money on anything else. I have been doing a tune up around every 3000-5000(ish) miles, oil, filter, plugs, wires, cap, rotor, points, condenser, air filter, pcv (which by the way sounds like a shaking paint rattle can at idle). I'm going by memory but I think I gap the plugs at .035, points at .023, all pretty much what Haynes says. Haynes says to set timing at 5 degrees btdc but I don't think I can use that spec due to the larger cam. I use the dwell on the gun, set at (aprox~between) 15 and 16 tdc,( not sure why, other than the car runs best set there, no dieseling, pinging etc). I've replaced the vacuum hoses and I do want to check for leaks (intake/carb) but I'm not really sure how, I think I've heard something about spraying with starter fluid or something but I would find out how before tryng.
I am still in high school and don't have much of a job but I'm willing to spend some on my car. I'm trying to figure out what would be the best bang for my buck to achieve what I'm after. I'm sure my dad would pitch in if I like paint the barn again or something. I just worked off a rebuild on the tranny! I have an extra Holley1920 (in pieces) and I plan on trying a kit rebuild BUT I want 4 bbl ooomph.

Also on a different note, my trunk leaks like a *****. Not sure where the water comes from and have even gotten inside with a buddy spraying a hose around lid, window etc, but never saw a leak. My trunk lid does have a rotten inside corner but don't think water is coming in there.