Which software solution is right for my goal (listed with specifics)

[wakasm]

Having been in a similar situation (I knew nothing about multiboxing before I found this website), I can't say enough great things about ISboxer. (Personal Bias!)

If you can't get all that you want done (your list) by the end of the free trial, then boxing might not be for you since ISBoxer is that easy to set up and work with. The Wizard alone saves so much time. You literally should be able to get 90% of what you want done in 20 minutes assuming you have your accounts set-up and characters created.

I went from 1 toon to 5 toons in about 2 hours, and within a day was able to multibox my first dungeon. I've had more challenges learning new classes and setting up in-game macros than 90% of how ISBoxer works. Everything you've listed, in terms of difficulty and set-up, is at the lower end of the spectrum of difficulty.

And like @Apps said - if money is an issue and you really have no desire to do anything more complicated than you have listed... you can do most of what you are saying by just opening two clients and alt-tabbing and just putting one toon on /follow and only switching back to turn in quests etc. Or use one of the free software solutions.

Just be forewarned: You will quickly want to try more than 2 characters once the concept of multiboxing clicks. The curve from going from 2 to 5 is minimal.

If it helps - I am 30. Referencing that since you listed your age.