In a Timber stand improvement that is aimed at transitioning from a high-graded woods to a healthy woods, some of the shelter wood/seed trees that were hopefully 10-16" in diameter at the time of cut should be ready for harvest 15 years later, just as the new growth saplings hit that 10-15' high stage, opening things up just enough for the sun to create a whole new crop of seedlings. Taking the largest half of the shelter wood out and doing the rest 5-10 years later can help the transition into a healthy forest with all three sizes of quality trees in even numbers.
The key to managing a woods with the least amount of sweat and chainsaw work is to carefully plan ahead to be able to have enough of some kind of trees that a logger wants, in order to entice the logger to pay you to come out and do your habitat work.
Clearcut is a bad word for deer habitat, and in a clear-cut that idea of logging in stages to constantly have food, cover, and saw logs unfortunately doesn't work, and this leaves two very harsh choices, #1, let your woods turn into a food desert for the next 30 years until you clear-cut again, or, #2; get out the chainsaw and do your own timber stand improvement on the saplings that no one wants.
To do a timber stand improvement on the saplings that no one wants, get a roll of orange flagging tape and mark the most high quality trees there are, every 50 to 100' in every direction, and cut all of the others down, trying to throw them on piles with a pole pusher so that the deer still have trails to get through. If there's no trails, take the saw and cut some. No trails in a cut saplings jungle creates a deer desert as well. Doing this above mentioned project on one acre only is an all day job for two strong, able bodied men, 100 acres equals 100 days, but guarantees good habitat. An alternative is to get a machine in with a chipper/mulcher head on it to save the labor.
Doing enough chainsaw work for habitat improvement to really make a difference is very hard work. The biggest joke in habitat work is when an "expert" is on TV with a 10" hand folding saw doing habitat work, declaring that they are making a difference. A herd of deer eat sprouts by the ton during the winter, not by little handfuls.