I live in St. Simons year round. The good - it is really lovely and charming. The people are polite and friendly. For the size of the town we have a great selection of interesting restaurants. The weather is great for about 8 months out of the year. Property taxes and home prices are reasonable. Lots of outdoor activities - golf, fishing, boating, kayaking, miles of bike paths.
The not so good. Flood insurance concerns are very real especially since we are at the whims of random flood map changes and legislation. Actual floods are less of a concern as most storms tend scoot by us and hit NC. If we do get a direct hit the entire island will be in trouble. Being one or two feet above flood level will get you a lower insurance premium but is not going to stop you from being effected by a direct hit.
There are some talented Doctors here but the hospital is not great and many people go to Mayo in Jacksonville which is 70 miles away.
Summers are ridiculously hot and humid. You walk out your door in morning and the humidity literally envelopes you.
If you have allergies or breathing issues the humidity and all the plant life will eventually cause problems. Even if you don’t currently have allergy issues many people develop them after they move here. The allergist is the most popular guy in town in the spring.
Finally, the bugs. Many nice days are ruined by our aggressive biting gnats and mosquitoes. Thankfully they are not year round and the sea breeze helps keeps them at bay. Most people have a pest control contract to keep termites, roaches and spiders out of their homes.
Honestly, the only thing that bothers me is our horrible summer heat and humidity because it often last until the end of September. I always hate when my Northern friends are leaf peeping and making stew and we are still cranking the air conditioning.
Let me know if you have any questions.