Formerly known as the Confederate Air Force, the Commemorative Air Force would be a good place. I don't think you could make much of a career out of it; the members I know are all volunteers. It would be a cool way to spend a weekend though! Good luck! http://www.commemorativeairforce.org/
I have flown one of their B-25's many years ago. It was with the organization for 6 years before I was able to fly it, and at that I was only in the right seat. Many of the pilots that fly the heavies are airline pilots or retired war vets that have lots of experience in heavy equipment.
Bring money and lots of it to the CAF. In order to fly, you must be an airplane sponsor. For the DC-3, it's $3500 and then it's DOC for training and currency flights. Flights to and from airshow's are rotated between all the elligible flight crew at no cost (cost is paid by the airshow event).
I have been lucky enough to fly more than a few. I put in a ton of time working on the local airshows and over the years got to know many of the owners. Each and every one of them invited me and other members of my crew out of appreciation for the help we gave them and for our commitment to the events. I suggest you take advantage of oppertunitys to get involved and to show long term commitment. Over time they will get to know you and things will just happen. I wouldn't even hint at your desires, they get that kind of thing every day.
I was very lucky in my B-25 time and to date it is the coolest thing I have ever flown. When ever I am in So Cal I try and stop into the hanger for a visit with the boys, who rememeber me no matter how long it's been. Maybe some day I will have the time to join you.
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