Yes he can be hard to understand. I think there are several reasons. One is his deep spirituality combined with an earthly no nonsense approach. He says exactly what he means and answers questions and church problems harshly at times, whilst always remaining in an attitude of adoration and thankfullness to God. This is hard for us to understand as it sometimes makes Paul seem a little superhuman. He even tells us to imitate him so he is aware that his life is clean and honorable unto God at all times. He seems a "cut above" the rest of us mere mortals and then he destroys that image by sayng that he wills to obey God but his flesh is weak. He also hints at a physical disability that despite prayer the Lord has not removed from him.
Personally, I see Paul as a rather stubborn man, one who always had great zeal for the Law, for the honour of God and remember he used this zeal in great persecution of the "people of the way". I think he would have retained that same zeal and same personality after his conversion, tempered by a love and peace that he had never before known and a daily walk with his Saviour and Lord. He would have been angered by laziness and and any slack in those who has come to faith. He was prepared to allow for new birth babyhood but expected believers to come to maturity in fast time. I think he was saddened by people very often and so very hard on error and also slackness but he kept a joy and thankfullness about the people he was in any way instrumental in leading to the Lord. In personal relationships I think he was the bossy type, remember how he "fathered" Timothy but he has a serious disagreement with Barnabus. Romans 1:5 ..this tells of how seriously Paul took his mission..No nonsense. he believed it his job to reach and disciple.
What is the Gospel Message..The ruling and reigning of our Lord and Saviour Jesus Christ in the hearts of men and later in time, in person from Jerusalem.(King on the throne of David)
I agree that Paul's letters must be read in context with historical information about the people, places and time he was writing. Reading Western 21st centuary ways into his letters can lead us to understand them poorly (not forgetting that the Holy Spirit is able to reveal His will and purpose to us no matter what language we read in or what the current year is).
I will comment on 1Tim3:2 about the requirements for an Overseer/ Pastor..a verse that many told me means exactly the english translation..that an Overseer/Pastor must have One wife....One wife. Does that mean he must have One, that is be married. Or have One wife, not two or three, or have One wife and have never had another, that is never been divorced. In this discussion in TheoChat I was assured by quite a few people of varying Theological views that this requirement means One wife, only ever One and as such means that no divorced person may ever become a Pastor. It certainly seems to read that way in our English translation. Not being satisfied that that interpretation fitted well with the requirement following; after all Paul is giving a list of requirements so they must tie together; I looked into this chapter 1Tim 3 and I came across a differing translation, which reads ..A congregation leader must be above reproach, he must be faithful to his wife, temperate...This is a very different statement to, husband of ONE wife and it carries well the requirements that Paul is making. verse 12 also speaks of deacons and makes a lot of sense if translated...Deacons must be faithful to his wife and managing his children and household well.
In context and in practise this translation fits the list of requirements that Paul is making and does not single out a phrase for special attention but rather makes a whole, a type of person who is right for the job. so is Paul hard to understand, Yes he is but we make him harder by our insistance on 21st century English intellectual understanding. We are even guilty of using our 21st century understanding of Paul's rules of conduct to bind ourselves, whilst proclaiming freedom from the Law, and Salvation and Conduct by Grace. Interesting thought..hmmm