Hayward is a good brand, no worries about that.
Cleaning filters isnt something you have to do all the time. The bigger the filter, the less you have to clean or backwash it. Normally only 2 or 3 times a year is required unless its extremely small. A 30 inch sand filter is a big one. A cartridge filter over 400 ft is a big one. A DE filter over 60 ft is a big one.
As for what filters best? I will be honest. They all do a GREAT job. When it comes to water clarity, the biggest factor is keeping the water parameters balanced.
If you keep your chemicals in check, you will be hard pressed to tell the difference in water clarity between any type of the filters.
I have a cartridge filter and I like it. I pop the cartriges out out (there are 4 huge ones) and spray them off. I use my power washer with low pressure tip to spray them down. Im done in 30 minutes. Its a twice a year activity for me.
As for the pump, there is no "one is better than the other". Disregarding the elctircal usage, it really all comes down to a personal choice.
With a VS pump you can increase or decrease speeds and doing that will change the current you see in the water, which I think is pretty cool.
Pumps should last a long time, 5 or7 or more years. Depends on how long you run it every year.
I like the VS pumps, but thats just me. Finanically it makes no sense, but being able to program the pump is the next best thing to having an automation system on the pool and gives me flexibility to add water features or a solar system in the future.
If there is a downside to the VS pump, is that the controls on it are sensitive to voltage spikes, power surges and such things. I would recommend that if you get one, to have the PB install a surge protector on it to protect the electronics.
An Intermatic PS3000 is what you would want to have installed.
http://www.intermatic.com/~/media/Intermatic/Documentation/Pool%20and%20Spa/Surge/PS3000%20Sell%20Sheet.ashx
Cost less than 100$ online. Im sure PB would increase that if he installs it for you.