Don - KM4UDX
Our local club (Vienna Wireless Society, in Vienna Va) has various nets almost every night in phone, digital, and CW). My humble v4 works well with all of them. But, getting a "SSB qso in the wild" is a rare bird. While listening to a contest, some island was calling CQ, and on a whim I answered, and I was floored when they came back to me. It was the first non-net qso. I was freaked and actually jumped for joy. (Getting out of the seat is good anyway, hahah).
The CARS idea is a good one. That also worked for me. I also stumbled once upon a Michigan net of retired automotive assembly folks. They heard me just fine. Participating in nets is a great way to go. Google the nearest radio club, find their nets, and give it a go.
lastly, while you want to keep the rig simple, just try hooking it up to any old laptop with fldigi. Just hook the laptop speaker out to the uBitx mic Jack, and uBitx audio out to into laptop mic. The world will open up. Totally. Digital modes (stupid name, they should just say "typing" or "text" modes) are wicked effective for our little uBITX rigs. If you just try PSK31 on 7070, and assuming you like to text chat, you will have a blast.
Let us us know how it goes.