Robert,

My husband taught me to fly his Luscombe, and he's not a CFI. It wasn't a
big deal. I think it depends on the relationship.

Other folks have mentioned insurance as an issue. That wasn't a big deal
with us, either. Buy the airplane that you, as the CFI, have the most
time-in-type in. That will keep your costs down. Try
http://www.auaonline.com/ for the best vintage rates.

Folks on our Luscombe List use their airplanes for "personal" primary
training all the time. It has been our experience that the high costs come
into play when tailwheel aircraft are rented out for commercial use.

Have fun!
Deb
--
1946 Luscombe 8A (his)
1948 Luscombe 8E (hers)
1954 Cessna 195B, restoring (ours)