Issues with a Skype contact for months

Alright, looking back at the chat logs, it looks like the issues began in April. There was a week of me trying to contact this guy. After that conversation that followed, I was unable to make contact with him for about 2 months despite his always being displayed as online. Coincidentally, it was when I installed the Skype for iPad app that communication was able to start up again.
We held some conversations for three days, and then there was another three month period of no responses despite his "online" status. I finally made it acknowledged that there HAS to be an issue, and sent a message or two to him after having installed the Skype for iPhone app. Coincidentally again, he got back to me saying he got the messages and thinks a problem is at hand. He hasn't responded to any messages in a month, and now he is never online at all.
I've tried everything I could. I've installed and uninstalled the Skype apps for both the iPad and iPhone and sent messages from both, I've cleared the AppData/Roaming/Skype info only to have the same results except this time with his avatar/name gone, I've cleared a great deal of the Skype registry info to no avail, I've installed and uninstalled Skype and even installed as far back a version as I could. Nothing seems to be working.
The one critical thing here is that I believe he uses a Mac/iPad as Skype mediums, not sure if he still uses the iPad app.
I don't think I was blocked, it seems out of character for this person to have blocked me. iPad/Mac related issues could be at hand, but that's no definite. This person may also have been too busy to have been online the past month, but he would have told me in the message he sent to me and there is still room for skepticism of that after months of this issue.
Any ideas? Even if I never get to contact this person again, this has almost become a challenge of sorts to see if I can solve the mystery of what has happened, it has become interesting somewhat in that regard.
Thanks.

Send that person an e-mail and inquire about it.  Otherwise it's all just one big guessing game.  You might also consider creating a new account, identifying yourself and request to be added under the new account. You never know if they accidentally blocked you.  This way if that person is available and wants to communicate with you they can.  If they don't they won't.

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