I think you may be overthinking the process. From your post I am assuming we are talking about a towered airport. In that case, I contact the tower at 10 miles out and give them a my call sign, what I am, position report, which ATIS I have, and my intentions. In return, they will tell me what entry and when to report. With moving maps you know where the airport is and thus the direction you need to take to enter the pattern where they say. Without moving maps, you have done your homework and know what the airport looks like and with dead reckoning should know approximately where the airport is. Usually when I am within 5 miles I can visually identify the airport and can then adjust my heading to enter the pattern based on the towers instructions. Prior to this I use landmarks I have previous identified to know the approximate location of the airport. If you do a proper preflight, and familiarize your self with the airport, and it's surroundings, and check the weather preflight, even without the modern conveniences of GPS, it should be pretty simple. If you are uncomfortable with it, would suggest practicing in real-life with another pilot or instructor, or with a flight simulator. At a nontowered airport the process is the same except you need to figure out how to enter the pattern yourself. I typically like to enter on the 45 to the downwind but occasionally sill over fly the field slightly above pattern altitude at midfield and enter downwind from there. Practice will help a lot. Also do not let a rude controller fluster you. They are there to help you, and use them as a resource. If they are rude, do not take it personally, just try to be succinct and to the point. If you are lost confess and even the rude ones will help.