I started out on a recip twin (Seneca). Single pilot, no auto pilot or WX radar. No GPS (GPS was just catching on). Two-three legs out in the morning, hang out at an FBO for the day... maybe take their crew car to the beach, use the FBOs fax to send resumes, then do the same thing in reverse that night. I averaged 75 hours a month. Like I wrote before, it was not easy flying ,but I learned alot. Nothing like breaking off an approach at night because the controller tells you there is HEAVY precip on the localizer and lightning is flashing all around, getting vectors, changing over to FSS for a minute to figure out the best route home, running the numbers in your head on the fuel to see if you can MAKE it home, then getting back to ATC for the vectors that FSS recommended, all while flying the airplane to improve your instrument flying skills. After 6 months they offered me a turbo-prop (MU-2), but I bailed for the regionals.
I heard about the job from a friend who heard from a friend, who heard from a best friend's aunt's boyfriend's mother.... you get the picture. I flew over to the airport where they were based the same day with a resume. The chief pilot had a 12" stack of them on his desk already. It was just prior to lunch, so after looking my resume over for a minute he asked if I wanted to go to lunch with the owner. I got the job. Right time, right place.
Did not worry too much about being furloughed as things were cooking at the time. When I hit the magic 500 ME time I had job offers/interviews left and right; even had an offer to fly DC-3s and the right seat of a Carvair ATL-98. Wish I could have taken THAT job so I could say I flew an airplane uglier than my grandmother, but with a kid running around and another in the oven the old "R" word (responsibilities) reard its ugly head. At the time it was not IF a regional would hire me, but WHICH one.
Feel free to ask any other questions, or PM me.