Tough call. I think you may have just missed the boat on the big hiring boom. The entry-level market has actually dried up quite a bit in the last few months due to cutbacks at the regionals. There have been furloughs, and there are going to be many more before it is done.

Both UAL and CAL have announced massive fleet cutbacks this week. I'm thinking that 5% of the current pilot force will be unemployed by the end of the year.

There is a little bit of light at the regional level. Majors can cut their own flying as much as they want, but since regional flying is contracted, they can only cut that so far without breaking the contract, or re-negotiating. I suspect that the regionals will not be hit quite as hard, but this could change if majors enter bankruptcy (voiding all contracts).

There are a few regionals still hiring, but I would expect competetive minimums to go up to 1500-200 TT with several hundred hours ME.

If you want to do this, you probably need to resign yourself to the fact that you will have to work as a CFI/MEI, and then do 135 or low-end corporate flying for a few years.

Maybe it will all bounce back soon, but maybe not. Oil prices are the problem this time, and it's hard to say for certain what that will do.

If you make the jump, keep your hand in IT so that you have income and a fallback job (I still do databases, and could do small-business network admin if needed).