Every person is different.  Generally speaking, you can expect to spend between 5 and 10 hours of dual instruction to get an endorsment.

No!  The tailwheel endorsement is signed off by a qualifed CFI.  It is up the the instructor to determine proficiency.  For futher information, see  14 CFR § 61.31(i) 

It can.  As long as the requirements of  14 CFR  § 61.56 Flight review are met, the instructor can sign you off for a flight review.  Discuss this with your instructor prior to starting. 

This is optional.  We will provide ground instruction prior to starting the first flight, as well as continuing instruction throughout the course.  Courses are available through 3rd party vendors such as Sporty's.

 Question of the Month.  How do I learn to fly a tailwheel aircraft - and what's involved?