It's my favorite way to hunt and I take advantage of any chance I have to do it.
If deer bed on the property you hunt, you have a chance. The difference on smaller tracks of land is you have to monopolize on the first encounter or else you will push the deer off that property. You wont have the opportunity to jump him over and over again.
The way I do it is to track really slow and with the wind in your favor. If you spook him the game is over. Basically it's still hunting while following a track. And make sure your ready for a quick shot.
It isn't easy, but it is by far the most rewarding method to kill a deer.