>>1153
Alright, let's break these down.
Paint: Fun, but not very helpful. Art doesn't sell very well so you'd have to spend a lot of time both in paint churning out large numbers of paintings (even at just three or four minutes per painting) plus exactly the same amount of time as non-magic artists on actually finding people who want to buy your stuff.
Wordpad: A little bit better than Paint because books and blogs still sell and plus they help you get ideas out into the world in a way that paintings don't. Still, mostly just an awesome toy rather than a life-changer.
Internet Explorer: Only useful under limited circumstances, circumstances any given reader is unlikely to ever be in. Sure, if you want to go into corporate or international espionage this'll make things way easier, but most of us don't want to worry about getting assassinated. It doesn't help that the connection is explicitly unsecure, not to mention unreliable.
Command Prompt: Really getting somewhere now. This gives you excellent health and while it's not explicitly stated, it seems like you can use it to reset your age. Keeping immortality under wraps so you don't get kidnapped by very wealthy/powerful people who want your secret is always a concern, but so long as you're not completely reckless you should be able to manage.
Calculator: Even without the program randomly changing notation, the fact that this doesn't help you avoid suspicion at all means that, much like Internet Explorer, it's only helpful if you already intended to make a career out of fraud. Skipping one dangerous, difficult step of a job that has multiple dangerous, difficult steps isn't really a big win because most of us are going to walk away from that job anyway.
My Documents: Very limited utility except to people in very specific circumstances. The photographic memory is a neat trick, but come on.
Minesweeper: So if you're pining for your ex-girlfriend who just dumped you last week, all you can do is confirm that yes, she still lives at her house until you get over it. This is only very intermittently useful.
Task Scheduler: This one could be real helpful. It's basically procrastination-be-gone, and it lets you work while you sleep, dramatically increasing your productivity in a way that isn't particularly suspicious. Sure, if someone actually sees you doing it then you'll get people asking you to teach them your mysterious ways, but if you live alone you can sleep-work for eight or nine hours each night and you claim you spend four extra productive hours working each night, when in fact you spend those four hours playing video games. People will marvel at your incredible nocturnal productivity, but not in a "magic is real" kind of way that might bite you in the ass.
System Restore: Oh, come on. There's multiple programs that are worth more than a thousand dollars on this thing.
In the end, I'd say Command Prompt wins and Task Scheduler is the only thing giving it any serious competition, although Paint and especially Wordpad are still painful to give up.
Advice for future revisions: Calculator, Internet Explorer, and Minesweeper aren't so overpowered that they need to be balanced by irritating or even life-threatening drawbacks. Let Minesweeper locate whatever the fuck you ask it to, let Internet Explorer be perfectly stable and secure (using dangerous information is risky enough without making acquiring it risky as well), don't make Calculator switch notations randomly when keeping your income under wraps is going to be hard enough already. And generally speaking Calculator needs a limiter to income other than "get too much and the FBI will take notice and throw your ass in jail," because that turns it into a non-option for anyone who isn't very foolish or a committed fraudster.