When I was young and invincible had a Long EZ and flew it VFR around the western desert regions (mostly) avoiding places where I'd hit anyone or anything. I went for a number of years without insurance on the premise that an accident that broke something that was repairable, I could repair for about the cost of a years premium. If it wasn't repairable then I was probably beyond caring. Well it worked for me and gave me plenty of "retract" time.
Stepping into the Mooney after that was not a problem. Too, first year's insurance wasn't too bad. It has gone down in the last three renewals but I think the retract hours, even though they were not complex hours helped. It also gave me experience in a fast airframe that does not like to slow down and will float a mile if approach speeds are high. (Sound familiar?) On the other hand, the EZ is simple to fly, gives a great view of the world, and a nice one can be had cheap. Get in good with an experienced mechanic at a local EAA club and you will learn lots about maintainence too.
Then again, most life insurance policies don't cover experimental aircraft and if you have family then stepping straight into a well maintained Mooney after you get your PPL is also a good option. You might check to see if you can find or form a partnership.
While I am rambling, two other things I suggest to new pilots are to check into getting emergency manuver training (can usually be done with a tailwheel checkout at the same time) and get a glider rating.