After reading a few posts here, I don't feel bad being new to multiboxing and having issues.

AutoHotKey
I'm not having issues as much as I'm unsure on how to script some things. I have a basic script that does some of the keystrokes I normally use in WoW (0-9, WASD, IWT etc). What I'm interested in is using Shift, Alt, and I'd love to be able to broadcast ESC to the other window. I tend to use Shift 0-9 and Alt 0-9 for modifier macros. Every now and then I may accidentally open a window on the second account when I forget to suspend AutoHotKey and I'd like to be able to just ESC to close it without having to mouse over to the second monitor / account. It's just me being lazy I guess. I also have a Logitech G510 keyboard with all those macro keys off to the left, is there anyway I can have AutoHotKey broadcast those to the second account as well? To be honest, that's not exactly important, more of an "I want" than an "I need".

Jamba
I have the latest version downloaded from Curse. As I have read elsewhere on this site I understand it's no longer supported by the original author but it's still functional. The issues I'm having are weird, so bear with me. The reasons for these issues may be related to my system setup and I'll be outlining it below. 1) When I setup Jamba and 'Push the settings' it shows as having sent them on account 1 and account 2 looks as if it's receiving them. However if I open Jamba the settings were not imported. 2) Both accounts try and set themselves up to the master, so I promote account 1 on account 2's Jamba and demote account 2 on account 1's Jamba. However, as I mentioned I need to have Jamba open on both accounts and set them up to keep the settings identical. 3) "jamba-follow strobeonme master" does not seem to function when I send the command on account 1. If I do it on account 2, 80% of the time the master (account 1) ends up strobing on the minion (account 2). When I do "jamba-follow strobeoff master" that will only turn off the strobing 50% of the time. If I fiddle with it enough I can get the master to stop following the minion, but it's a pain. It seems that even though I've manually told Jamba which is the Master (account 1) and which is the Minion (account 2) that it still thinks the roles are reversed. I've made a follow macro, but it gets annoying constantly having to mash that button.

2 Accounts / 1 PC
Here's where things are going to sound odd, and I'm afraid this is could be where all my problems are originating from. I have the Battle.net desktop app set to allow multiple instances of the launcher. I start 2 battle.net apps each with the login for an account and then I start both accounts from their respective launcher, they still share the same WoW directory though. So while it's 2 windows open on separate monitors they're both using X:\World of Warcraft. I'm not sure if I need to run account 2 from a different WoW folder. Which means I won't be able to use the Battle.net desktop app unless I can install a second copy of that to a different folder too. Having both accounts utilizing the same files has me wondering if that's why I'm having issues with Jamba... since they'd both have the same files open at the same time.
The nice thing about using the battle.net app is that I only have to enter my authenticator code every few weeks and, of course, it notifies about any updates to WoW.

All these issues aside, it's been a blast running around on two toons at once. lol. I'm currently doing 2 DKs and have made myself a pair of monks to do next. Melee toons are a pain, getting both in melee range and facing the right way... that's just the way it goes I guess. I have some fairly bland macros for fighting, so if anyone has any that are better, I'd love to hear them.
As it stands now, account 2 has macros to assist account 1 like so:
#showtooltip
/target focustarget
/cast [@focustarget ] Spellname

I was wondering if maybe I should change the /target focustarget to something like /assist Party1. I've noticed that /assist will dismount you even if you're not in range of the target which is why it's not built into the macro. I know it also seems redundant to have the /target line there with the @focustarget condition but I like to make sure that account 2 has the target before attacking. (i.e. running towards a mob but not in range to attack).

I'm sure it's obvious that I've only been at this a couple of weeks now. So I just want to thank you for the at least taking the time to read the post and for any answers / suggestions you have. I'm going to be sticking with AutoHotKey as it is free. I know about ISBoxer but this is more of a 'fun thing to try' for me so I'm not looking to pour cash into this.


Dakkar.