1: Anyone can claim anything, doesn't mean it will stick. The fact that he stated he has owned it since this year shouldn't make any difference in a UDRP case, what will matter is how HE uses it. IE he needs to make sure any parking page doesn't use terms or ads that violate a tm, especially in the country he is trying to target.
2: See point in number one... yes anyone can do/say anything. If he finds that someone has filed a TM in order to reverse hijack the name, he needs to make sure his ads/content doesn't infringe the new tm. If his use of the domain predates the TM, it should work in his favor if they decide to UDRP after the fact. Perhaps someone with more experience or a lawyer can comment on how to handle a reverse hijacking attempt.
3: Again, see point in number one. If he files and gets a TM and uses it for that purpose, he will/should be protected for that/those uses. If he were to change it's use to infringe on another TM, then he can't say he has a tm so hes ok... hes not, he is now infringing. Also, at least in the US, you have to show use in commerce to get a TM... so just filing for a TM (at least in the US) without usage will not be granted...
1. YES!!! Bad move. Many UDRP decisions are considering change of ownership as a new registration. So you don't go around advertising it..
Damn I thought I will be safeproof by buying aged domains..
As long as the complainant doesn't notice the registrant change, you are safe...
"Safe" is relative to the intelligence of the arbitrator..