I would drill one hole, if you really don't want to drill two, and use a
diplexer. Cable losses are worth saving for that - its no big deal drilling a
hole - much more of mounting aerials safely.
Even better drill a 30 to 40 mm diameter hole, sleeve it with waste pipe, then
run whatever cables you want, when you want. I guess you won't like that though
!
Always use good quality cable - its a cheap "upgrade" - no point in spending
500 to 1500 on a superb rig and wasting half its power in cable losses ! UR67
or RG213 at least - in UK I use Wesflex 103.
A power supply is a good investment - secondhand they are not expensive, but
many use batteries and chargers so its an option.
Wire it up safely ! Fuses where appropriate etc and thick power cables to
minimise losses there - no "bell wire".
As the other poster said - borrow the ARRL or similar from the library or buy
it new or secondhand - the contents don't change too much too fast........

Hope that helps,

Welcome to Amateur Radio !

Nick