Tell me what you would do. (new /old job possibly)

[Hiptotorus]

Sounds to me you are missing a consideration of this whole thing.  

A new employment is a negotiation.  You haven't signed anything yet.  

So figure what you "Have to have" and settle for no less.  If it's a monetary value then that is what it is.  If it is job security then that is on the list.  Vacatation time, sick days, holidays, health insurance, resources, capitol budget, hardware, education, certs,people to do the work for you... But this list has to be non-negotiable.

Then write a list that is "I would like to have"  and one of "I would settle for" These are the negotiable points.  I am not sure if Ohio is a right to work state or not so for the job security part of it you may want to consider putting into your employment contract something to the effect of "if you screw me again by firing me I want 6 months severance"  You may need more legal sounding terms though. :-)  Now these two list and the things on them can not be on the "Have to have list"  So if your willing to accept less money then money isn't a "have to have"

Once you get it straight for yourself then it's just a business meeting after that.  Walk away if everything on your "Have to have" list isn't satisfied.  Worst case your life is the same and the grass isn't always greener on the other side.

My 0.02
 

[Kith]

While I agree with the whole "do what is going to leave you happiest at the end of the day" mentality (I had to make the same choice once), there are two other points that have popped to mind:

1.  If you were to return to your Mac support gig, (which it sounds like he is willing to let you back thru the door regardless of how much you've kept up on certs and whatnot), that would be a good way to start rebuilding your own knowledge base if that is something that you would like to get back into.  Additionally, once you have a good feel for the current software and so on, you could probably get them to pay for some training or certifications.  Aside from the benefit of actually learning the stuff, if the IT job goes belly-up you can at least walk into future interviews with a list of fresh certs on your resume.

2.  I've heard you talk about the dude you work for now and how he doesn't seem to be a very shrewd businessman.  I have to wonder how long your efforts and his luck will last before he makes a catastrophic mistake and the pizza place implodes.

Sounds to me like you have a good idea though, talking to the guy who works for him now.  Good luck!

[Turkley]

After you talk to this guy who works there now after leaving and going back, and he says everything is cool and stable, I would seriously consider it.  I would try to get as much money out of the old boss, up front, as possible.  I would also make sure if is 100% aware that you could be a bit rusty, having not worked in that type of position is quite some time, while also telling him that there isn't anything you can't learn quickly and efficiently.  If he is cool with that and willing to "cut you some slack" persay, I would definately consider it.

I can say from my personal experience, that I have left jobs I hated for less paying jobs, that didn't seem to be as secure and it worked out ok for me.  Granted that was my experience, and I have gotten very lucky thus far in my career choices, but it all has worked out well so far.  In the end, you just have to way the options and see if the risk is worth the potential reward.

[ch0wdah]

Rocky's has all things that are good.  They've got Bailey's.  Do you love me?

[Volk]

First off, if you hate your current job, find a way to get out of it. Second, how much does your old boss want you to come back, and how much is he willing to shell out for your skills. And C, is it something that you would be willing to go back to if you can't get the pay raise/pay matching of what you do now.

[Jim Tressel]

Follow your heart, that's what I always do.  Or you can follow Chuck to the promised land.