Ask HN: When is risk worth it?
Alright, so I'm in no way a talented coder or even very technically savvy (much more of an admiring "coder wannabe" actually) but ever since I first stumbled on a PG essay on philosophy (in the midst of a typical googling/reading binge) a year or so ago I've become a daily troller of the HN site. During this time, I've become an avid reader of numerous tech blogs and have a huge appreciation for the way you guys process ideas and your thought processes in general. That being said, I would very much value some opinions on a (happy) career crossroads I've found myself in.

The short on me: I'm a 27 year old, hard working clincal coordinator for a mid-sized private medical practice (by hard working I mean hours don't phase me, I work for the clinic during the day, and split my nights and weekends between a free clinic and waiting tables.. student loans rock!). A 70-80 hour work week is pretty much a standard, and I'm fine with that.

My dilemma: My current job at the clinic is great, I initially took the job to help out my dad, who runs the practice and was short staffed..and ended up loving it. I've worked my way up from a tech, managing 2 clinical trials, to now running 2 of our satellite offices and being in charge of all of the IT stuff (part of my obsession with HN!) I love the doctors and patients I get to work with, and have been experiencing a steady rate of growth, both in pay and responsibility within the practice over the last 3 years (They even put up with and give me free range with our old servers for testing out ideas I have with record sharing.. it's great!)
At the beginning of this year, I got fed up with the horribly arcane way we were tracking inventory and monitoring expensive drug ordering/usage across our 6 offices (literally, sticky notes and texts passed here and there)and decided to write a little program that would allow us to keep track of drug usage/inventory levels and reimbursment periods across all the offices in real time. It ended up working pretty well, and one of our docs ended up showing it off to a drug rep we worked with, who then borrowed it to use as an example for other practices(yay!)
Now I've had a few offers from other practices and an EMR company, but haven't been tempted away.. until now. I was contacted earlier this week by a practice in the city I grew up in (and have been wanting to move back to) and asked if I was interested in taking the administrator position with their practice. They are wanting to implement an EMR, update 5 out of 6 of their offices (two do not have internet!), reorganize their practice structure and create/implement a marketing plan. Immediately my brain was spinning, by the end of the week I had talked to each of the partners individually, written out a few plans and was pretty excited about the opportunity. They gave me an offer Saturday, saying they'd rather fly me out once to look for an apartment and get to work than twice to meet me first because they knew they wanted me.

The catch: Before recieving an offer, I met with my dad, who has been doing this for the past 30 years, as well the main Doctor I work with. Both agreed it would be a great opportunity for me, and said I should jump on it.. on one condition.. they offer $X (the min salary for someone in that position, also the bottom of the salary range that my dad had actually given this practice a year ago when he had done some consulting for them and they were looking to fill this same position) I felt this number was a little high for my experience, however given the amount of work involved an the significant increase in cost of living, it's actually pretty reasonable. Their argument is that the dollar amount shows they are serious about the relationship, and that they would be supportive in future efforts when it comes to updating their systems.
They offered significantly less, actually almost less than what I currently make at both jobs (total hours worked would probably be about the same) I was disapointed, but declined the offer, heeding my dad's advice. They called back today with a slightly higher offer plus an incentive once their EMR is implemented, the total is still less than the original target, but enough that I will make a little more than what I make now..although most likely be working much harder.
They seem like good guys, they've promised that the compensation will increase and surpass my goals once I've proved myself and as my skills mature. The opportunity alone excites me due to the sheer challenge of pulling it all off and the experience I would gain along the way, however it's still definitely a risk, the practice is challenged and I could always fail badly. Additionally, my dad and the owner of the current pracice I'm with have advised that since they failed to offer an acceptable amount from the beggining, I need to move on, arguing their offer shows they aren't serious about changing the organization and I would end up frustrated and set up to fail.

I would like to know, in evaluating your own job prospects, what makes the risk of a new opportunity worth leaving a safe and stable one? Currently I'm very happy where I am, and am able to "incubate" and grow my skills safely, to the point where in a year or so, the target salary given to this company should be quite easy to obtain. This new job though, while a huge risk, could be a sweet experience that lets me test what I can really do..or can't do, which could undue the gains I've made over the past few years?? I'm extremely conflicted, tired from all the negotiating (so please exucse the grammatical inadequecies!) and this forum has proven to be source of level headed discussion on a variety of topics, so I would greatly value any input/or stories from people with similar experiences.
Thanks for taking the time to read/respond!