Holding patterns
You need to be sure that your student understands holding clearances. Maybe that's the root of the problem.
For one thing, your inbound course is always to the fix. Students tend to misunderstand that if ATC clears them, e.g., to "hold North of BONEHEAD on the 360 radial" means that the inbound course to BONEHEAD would be 180 magnetic. An idea to try is to make that point clear and have the student draw the actual holding pattern on the chart while going through each component of the clearance. A common error is students are confused about which way to turn in a standard racetrack. They seem to think that a standard holding pattern has left turns, probably because a standard traffic pattern has left turns. So, before you go on to teach them standard entries, be sure your students are clear about inbound courses and the correct direction. Theoretically, ATC is supposed to state if the pattern it's clearing you should have left turns; otherwise, you assume that the racetrack is to the right.
One other, vital point about holding clearances: Make sure you get an EFC time from ATC in case you lose comm. A very common error in training is students won't demand an EFC time if "ATC" (meaning the CFI-I) doesn't provide one in his "clearance."
Once your student is clear about his holding clearance, then you can help him with entries. Despite what others may say or believe, your student needs to enter holding per the AIM. The AIM is the FAA's preferred way of doing business. Although the real world may be different, most examiners will expect students to enter holding per the AIM.
I learned a great way to visualize holding when I was a Riddle instructor. You spread out your thumb, forefinger and middle finger of your hand and place your hand on the HI, with your forefinger on the lubber line. Right hand for a standard pattern; left hand for a non-standard pattern. The area between your middle and forefinger is for teardrop entries, between thumb and forefinger is for parallel, and everything below is for direct. The line from the bottoms of your thumb, forefinger and middle finger is the 70-degree line. So, if you understand your holding clearance and place your hand as I just described on the HI, you'll see your FAA-mandated holding entry. Now, if you have an HSI, it's a bit easier. Set the head of the arrow on the HSI 70 degrees down from your inbound course. Don't forget, if your within five degrees, I believe, on the borderline between one kind of entry and another, you can use either one. Of course, the idea is to enter holding within protected airspace.
Try working it out on paper with your student before trying it.
Wind correction on the inbound course is just like wind correction for tracking. Whatever keeps the CDI centered. Fine corrections as you approach the VOR. Outbound, try doubling your correction. You may have to go around the hold a couple of times to nail it. Unless you know you will have a really strong tailwind on the outbound, go out a minute, as the AIM recommends, and see how long it takes for the inbound. Increase or decrease the time on the outbound as necessary until you have a perfect (more or less) one minute inbound leg. Of course, if you have to depart holding at the EFC time, you adjust the outbound as necessary to hit the fix inbound at the EFC.
I'd say the basic philosophy of holding boils down to understanding that a hold is based on a basic four-minute racetrack with a one-minute inbound (I realize a 1½-minute inbound applies above a certain altitude or FL, but I don't recall it at the moment), understanding the elements of a holding clearance, and being crystal-clear on what comprises the inbound course. Once again, your student should never forget to ask for an EFC time if "ATC" doesn't give one.
Try simple examples and make them more complex as your student starts to "get it." I'd go back into the sim to hone his skills before returning to the airplane.
Hope that helps. Good luck with finishing your student.
