I think the $30 kit is OK, but Im not really sure you need the professional grinder brush or the espresso cleaner. A $2 pastry brush looks just the same and does the same job. The espresso cleaner is effective, but I think dishwashing powder is pretty similar and a lot cheaper. I did buy some of the espresso cleaner.
Im all in favour of the blind filter and the group head brush. The Pallo coffee tool for $30 might be a better toy. A pastry brush and a small paint brush(like for arts and crafts) for the grinder is cheap and easy to get anywhere.
The blind filter is $5.75, the standard group brush is $7.50
I dont do a chemical backflush very often. Only done it twice in fact.
I do a water backflush weekly. I also take the shower screen off and clean it and the group. A Short flathead screwdriver is required for this.
I soak the portafilter and baskets in a solution of espresso cleaner/water. It works very well, but as I said, seems pricey for what you get.
As for the gasket sets, pickers etc. I have not had any need for a gasket replacement as yet. I have a spare set, but from what I have read, it can be a pesky task. I doubt that you will need to worry about gaskets for a while.
As for daily/routine stuff, wipe the wand and purge after doing milk (non-abrasive cloth). Send water through the group pre and post shot making. Wipe down and empty drip tray as required.
Hope that is useful.