Lowtimer,
Our group (which has been running successfully for at least fifteen years) regularly has new members with less than 100 total time and we have also had a student in the group, although this did increase the insurance slightly. The group has six members and one or two shares seem to change hands each year.
We require a checkout on type and if the new member hasn't flown taildraggers, the conversion is done on the group aircraft, taking as many hours as necessary- normally at least five.
The group is run so successfully that we have just been able to have our engine zero-timed (After 2600 hours).