Once upon a time, say two or three years ago, you could just invite people over and serve anything you wanted. Nowadays, everyone is on a special diet. It's to the point where cooking for a vegan is the easy part. It's making everyone happy that is a struggle. The most difficult menu I ever did was for my parents' 40th anniversary. Over a dozen attendees kept kosher, and at least that many would have been offended if they were only offered kosher food. What I finally did was present two different buffets. The dining table was all kosher dairy, while the larger one on the patio held everything, kosher or not. And everything was labeled. Of course, since I don't have a kosher kitchen, it wasn't truly kosher anyway, but the guests seemed satisfied. You can't explain to some people that "kosher-style" isn't actually kosher.
When making a guest list, consider the nature of your gathering and who would appreciate it. Not a drinker? They won't enjoy a wine-tasting. I don't invite men to my teas, even though they would probably have a great time. It's a bit too much of a girlie thing. Carnivores go to the top of the list for a barbecue. Then there's the mix of guests. Make sure you aren't having over people who hate each other. For holidays, I tend to invite the exact same people every year, but I mix up other gatherings. People who don't know each other have more to talk about and bring different interests to the table.
As for creating a menu around these interesting friends, family, and acquaintances.... I'm learning not to stress it. I do ask in advance if anyone has an allergy or other special dietary need. Then I make sure that any one guest can eat at least most of what I serve. If a vegetarian is coming, no more than one dish will have meat or fish in it. Low-salt diet means I add as little salt as possible to all the food and put a shaker on the table. Low-fat and -cholesterol, use lite and egg-white substitutes when they won't affect the dish. If anyone has a nut allergy, I either forgo nuts entirely or make it clear which dishes contain them and am very careful in the kitchen to avoid cross-contamination. As for gluten-free, I know it's a craze, but studies have shown that unless you have a wheat allergy or a sensitivity condition such as celiac, going gluten-free is actually harmful. I know I feel terrible by the end of Passover; maybe there's a nutritional reason. I'm perfectly willing to serve sandwich fillings on the side as a salad or make brown rice instead of stuffing, but traces of flour in sauce will not hurt the vast majority of people. Generally, people with complex diets don't expect you to create your entire menu around them and are happy if they can eat at least half of the dishes presented. And if the diet is not a life-and-death issue like diabetes, an allergy, or celiac, most guests will abandon their own requests if the food looks and smells good.