I too recently bought a house with a pool and have been reading all there is to know. It does get easier, trust me!
I had a similar problem and it also continued to be a problem when I bough a kreepy crawly too, there was basically no suction coming through when i hooked it up. To resolve, I have to do the following steps :-
1. Put vacuum plate into skimmer basket and test suction by placing hand over the hole. If it is low suction or nothing at all, check filter is running. If it is, then place palm of hand over hole until suction is created. This sometimes involves moving the vacuum plate around to create a 'snugger' fit!
2. After successful completion of (1), make sure all the air in the vacuum hose is expelled by using the inlet to the pool to push it out (don't forget to not let air back into the hose after completing this step)
3. Hook up vacuum
4. If it still does not work, check hose and vacuum head for blockage.
5. If it still doesnt work, throw a tantrum and go to internet!
Cheers