Here is what I suggest.
Get your CPL, ME Rating, hold off the IFR. Get your instructor rating. Instruct for 1.5 to 2 years, get yourself close to the ATPL requirements (make sure you do night ratings to get that 25 PIC XC NIGHT up), get your IFR, write the A's, get a turbo prop job with a lot more valuable time for upgrade down the road.
It may sound retarded at first, but PIC time is PIC time - and as far as upgrades are concerned when time comes for your King Air / 1900 days, PIC time is so much more valuable than SIC. I only say this because you kind of hint at being at a disadvantage at the age of 30 - which I don't agree with wholly, but depending on where you want to end up you may want to take the route that is the most efficient.
Get your A's written done, get on a 1900 or King Air somewhere, work there, and for a guy like you, a great career place might be Jazz which with King Air and 1900 time would be a very probable option. Corporate is also a great place to go too.
The reason I say you should hold off on your IFR is because after instructing, you will be teaching EX24 quite a few times. While you won't be teaching "IFR" necessarily, understanding what you are teaching in Ex 24 is going to make your IFR way more cost-efficient, and will click a lot faster than it ever would at 250 hours. Also, chances are that the school you instruct at will give you a discount rate on the plane/instructor for doing it in house - especially if they need you to teach their IFR side. I strongly suggest doing most of the "flying" in a single engine, and transfer the last 5 hours of IFR training (basically review) in a twin. This is where your multi rating from the past will serve as beneficial because you don't have to re-learn how to fly a multi again. One or two quick review flights, and you're at PAR and getting ready for your IFR ride.
This will save you tons in the long run and would be what is in my opinion a great way of maximizing the start of your aviation career.
Second chances are company oriented, and really, all these companies have "procedures" and "protocols" set in place, but as we all know, even though a company requires 500 hours multi to hire a king air f/o, they hire them with 30 hours of multi as well. So I am a strong believer that your work ethic will relay your success in this industry, whether you get let go after 2 years cause of a bad day or not. You pave your own way in this industry man, and if you think you've got what it takes, then do it bud!

Don't get plastered with the negativity on these boards - self belief is what it takes to succeed, especially in the aviation career. If anyone tells you that you can't do it or "don't count on it" it's because they can't and they have lost faith. There's a way to achieve your goals, and the way is as smooth or as shaky as you make it. People who get caught in their own negativity especially on these boards might have others to blame, but themselves as well. Be positive, keep your chin up, and most important than all - LEARN, and I promise you will succeed!
All the best
