If you are going to serious about all grain brewing you really are much better off with the 10 gallon set than the 5 gallon one. Any higher gravity beer is going to be difficult to fit in a 5 gallon cooler, and you will just find yourself wanting the 10 gallon coolers a couple months down the road. If you are a time is more valuable than money person then go ahead and get them pre-made. You can make them yourself if you are a little bit handy and have a some time. Here is a great link
https://www.homebrewtalk.com/f51/cheap-easy-10-gallon-rubbermaid-mlt-conversion-23008/
As to your choice of mill, it is a good mill with a good reputation. You will find no shortage of opinions on the best mill round here, but the short list usually includes the one you are looking at, The Monster Mill, The CrankandStein, and the BC Barley Crusher.
Unless you have a commercial gas stove you are going to struggle a bit to get up to a good rolling boil on a kitchen stove. A moderate propane burner set up gets you there much quicker. You don't need any of the super high 100,000 BTU burners, most of your run of the mill turkey fryer burners are plenty.
To do full boils you are going to want a pot with a little headspace to allow for the initially higher volume before boil-off. It depends on if you use foam control or not. Some get along with a 7 to 7-1/2 gallon pot. A 9 or 10 gallon gives you some more breathing room, and a 15 allows you to move up to 10 gallon batches in the future if you want.
As to software, Promash or Beersmith. Both great functional programs and I believe they are both free to download and try out. So download them and decide yourself.
