Here is the instructions from the manual on my cutter. Step 8 would allow the tail wheel to be in contact with the ground at all times during normal operation (except when the lift function was all the way up).
I think that all of them all have about the same instructions:
1. Park the tractor and cutter on level ground.
2. Using the 3-point hitch control lever, position the front of the cutter with the side skids 1” less off the ground than desired cut height. For example, for a 3” cut, position the skids 2” from the ground. Set the 3-point control lever stop at this position to maintain this height when raising and lowering the cutter.
3. Shut down the tractor and remove the key.
4. Adjust the cutter deck front to rear by extending or retracting the 3-point top link. Always set front of deck 3/4” lower than rear for best performance.
5. Level the cutter side to side by manipulating one lower lift arm length. On most tractors, at least one of the lift arms is designed to allow for manipulation of its length. Shortening or extending will allow for deck leveling from side to side.
6. Securely block up the cutter at this height.
7. Remove the bolts securing the tail wheel beam in position and allow the tail wheel to rest at ground level. Align tail wheel beam between nearest sets of holes in beam support brackets and reinstall support bolts on each side of beam. Tighten all bolts and nuts.
8. Extend the tractor’s top 3-point link so that when lifting the cutter, the front of the deck will raise 2 to 2½” before the tail wheel leaves the ground. This will allow the cutter to follow the contour of uneven terrain.