No problem - your setup is very, very similar to what I had when I first started - I had a Fluval 205 can on my 20g tall before I got a GFO reactor and also had a HOB skimmer. The best investment you can make is buying a sump that'll fit under your stand - even if it is only 5 gallons. I put a 10g under my tank and those extra 5-7 gallons make a big difference for keeping things stable. It also makes it easier to get a much bigger skimmer, a quality ATO, etc. as you grow and get better equipment. Before spending any money on upgrading things you find lacking, get a sump. You can only go so far with HOB stuff and it takes up a lot of space.
Don't worry about not having a drilled tank either - the CPR overflows work great and never fail as long as you keep a pump on it in case of a siphon break. Just keep up with your maintenance, keep a watchful eye on the tank and be patient - your tank will age and your problems will pass.