A man who was on travel prayed Duhr as four Rakhas upon leaving Tafilah heading to Amman. However, on his way to Amman, he prayed Asir as two Rakhas (Shortened). Is what he did correct from an Islamic perspective?

Does wiping over one's socks during ablution permissible?

If the socks were thick,  then wiping over them during ablution is permissible so long as wiping conditions are observed. And Allah Knows Best.

I suffer from chronic asthma which requires ventoline inhale; which is an air causes the risperatory track/airways to expand. Am I permited to use it during the daylight of Ramadan? And does break one's fast? Noting that I can't go an entire day without using it?

Taking inhaler through the mouth or the nose breaks one's fast, because it is meant to reach the lungs which are part of the coelom. Therefore, whosoever use inhalers for couple of days is obliged to preserve his fasting and make up that day later. As for the ones the ones who need to use it every days are obliged to preserve his fast and feed a poor per day and the cost of feeding one poor is estimated (60) piasters for the year (1421AH). And Allah Knows Best.  

Is it permissible to offer mandatory prayer while sitting?

All perfect praise be to Allah, The Lord of The Worlds, and may His Peace and Blessings be upon our Prophet Muhammad and upon all of his family and companions.                                                                                                                                                                                                                            Standing up is a pillar in the mandatory prayer and the prayer is not valid without it unless one cannot do it. As for Nafila (supererogatory prayer), one can perform it in the state of sitting even if he/she can stand, but his/her reward is half the reward of the person who prays while standing if he/sh has no legal excuse for such an act. And Allah Knows Best.