Unfortunately sewing, like any other hands on craft is not really something you can learn from books or the Internet. You are best off finding a good open minded sewing teacher with supportive classmates. Personally I take private lessons in a group of 3 and the teacher ensures that my classmates are open minded enough to not care who I am making the skirt for. Hey we don't even have a change room so if you are going to fit something you need to wear nice knickers

Gore, the shape and turning 2D into 3D are only part of the problem as the fabric that you choose will make an incredible difference to how the garment looks and feels. For example clothing made with stretch denim will behave very differently to silk or delicate chiffon. Taffeta (think ball gowns) is a real pain to sew as it shows every crease or defect both in the garment and the wearer - mind you if you have the body and fit to pull it off it is stunning.
The next variable with skirt making is fit v ease of movement v difficulty in wearing. For example a mini skirt provides great ease of movement however you always have to be careful how you wear it not to expose yourself. A pencil skirt if too tight will ride up (again care with wearing if above the knees) and is difficult to stride in (think ladders and stairs), A line skirts tend to provide a reasonable compromise BUT if the A is too wide and you don't have large hips it will not fit well and tends to look "girly" as it emphasises the hips. Long skirts present even more problems as flowing skirts tend to be high maintenance (needing to tuck in the fabric, avoiding looking like a tea caddy, not tripping over the fabric when climbing up stairs or over rocks), pencil skirts severely restrict movement (think penguin) and require a slit which tends to look feminine (unless you personally go for the peek a boo look with your legs). One solution is to put a kick (a wider part around the lower part of the skirt) but again, too much kick and you will look "girly".
To date I have solved the problems with knee length skirts for me (and I happen to have round hips so women's clothes fit me infinitely better than mens' clothes) but have given up on longer skirts as I cannot find the balance between comfort, fit and ease of movement. Mind you I am rather conservative and don't like to look at all feminine and tend to be influenced a lot by my family and sewing class's opinions.
The easiest skirt to make is a wrap skirt - firstly it looks like a lava lava or sulu (islander skirt) so people CAN put you in a box that doesn't say TV/CD/Pervert, secondly it is easy to fit, thirdly if you make the wrap wide enough you can move freely without showing anything. I recommend the Burda 8278 (if you go to a sewing shop and ask for that you will get the right pattern) modified if necessary to allow for a smaller waist to hip ratio (put simply enlarge the waist by several inches and bring in the hip as most guys don't have curves). You may also want to increase the wrap length (and corresponding yoke) to make it easier to wear.
Good luck.
Dave