(First Post!)
Anguilla is awesome but not without its flaws. First off it is maybe my favorite Caribbean island because the people are incredibly sweet. I went every Christmas for about five years and have family who went for about 20 years. Last year I went back after a 10 year hiatus and it was like nothing had changed. Locals (non-hospitality) remembered my name and asked about my family. The beaches are great but local architecture is rustic. Apparently you didn't have to pay property taxes until your home was finished so, brilliantly, no one ever added the "top floor" of their houses. As result all of the houses have rebar sticking out of the roofs. I cannot speak to renting a place the resorts are great but ridiculously expensive. I stayed at one place that was really low key but they used it as the set for a Fox reality TV show so I am not sure of its current status. If you would like I can find out the name for you. Further, the restaurants are insanely expensive and I live in NYC. There are cheap local places that are awesome but take a bit of local knowledge. One other funny thing is that you drive on the left side of the road with left hand drive cars.
I don't know about is getting on island. I am not sure there are commercial flights direct. Flying into St. Maartin and transferring to a puddle-jumper is easy or you can take a ferry from the French side. The airport does accept large private planes so maybe there are more options.
I will go again at some point. Have a great time and tell Banky, Elvis, and Carrol I say hi!
Neil