Proper Technique and Duration for Lower Lid Massage?

Dear Dr. George
One finger, two finger, three finger. At four months after surgery it does not matter. Your are going to need a repair of the lower eyelid. Messaging the right lower eyelid is going to make no difference in the appearance of the right lower eyelid at this point.
Yes Dr. Cassileth is correct regarding factors that predisposed you to heal adversely following a transcutaneous lower eyelid approach to the floor of the orbit. However, even with a good cheek bone projection, this particular approach is prone to poor outcomes when the lower eyelid heals related to the fact that the surgery invariably created an adhesion between the orbital rim and the middle layers of the lower eyelid. Your particular bone anatomy just makes this a bit more likely. For these reasons, oculoplastic surgeons tend to approach the orbital floor through a swinging eyelid approach at the lateral canthus an avoid violating the middle layers of the lower eyelid.
To fix this, you need a surgery that is almost only performed in the United States: lower eyelid reconstruction with hard palate graft and possible ePTFE orbital rim implant. I invite you to look at my website: lidlift.com to see example of this type of surgery and also read a detailed discussion of the procedure.
You might consider contact George C. Charnois who founded the Athens Vision Eye Institute in Athens and see if he performs this type of procedure. He trained in the United States and did his oculoplastic fellowship at the Jules Stein Eye Institute and did train in these methods.

One additional consideration is to have steroid injection into the area and continue your lid massages. The steroid will help to soften some of the scar tissue so that the lid massages may help to reposition your lid.
Other options for your problem include subperiosteal dissection of the orbital rims and microstructural fat grafting to support the lower lid and also reestablish some fullness in your depressed cheek bone.
ePTFE as a orbital rim recontructor offers a significant risk of rejection which should be considered prior to committing to this technique of reconstruction.

I would keep trying for at least two more months. I personally place three fingers flat on the lower lid and push them upward so that the lower lid covers part of the iris. Check your normal side - it should easily push way up to past your pupil. You look like you have what we call in the industry a " negative vector", meaning your eye is more forward relative to your inferior orbital bone, and this sets you up to have this problem. Don't pinch and pull up as this can stretch your lower lid and create laxity, worsening the ectropion. You may need a procedure to release the ectropion - what procedure depends on the severity on exam.