Brent, I don't know of a time of year to avoid Biloxi. Hurricane season causes some anxiety, and once they had to evacuate Beau Rivage shortely after we left...was it in March, April? I can't recall, but it didn't affect us and seems to skip that location often though they make it look like it on the news maps.
We stay at Beau Rivage, an MGM property, which is lovely, was built by Steve Wynn to be a 'little Bellagio' and sure enough very much like it. Reportedly taken from Steve in a 'hostile takeover' by Carl Ican or somebody big in that business, which I don't really comprehend.
We get the charter flight offers which fly us to Gulfport, bus to Beau Rivage, they tote your luggage up to your pre-arranged room while you gamble some in the casino. Going home they pick up your luggage from your room (if you want) and stow it to the airport where you tote it to the check-in desk to be loaded on the plane. I don't know where you live, but there may be something similar from where you live. Free flight, free rooms, some Free Play and other perks. Sun Country airlines.
Biloxi has "Beach Boulevard" running in front of BR as the main drag leading to other casinos including Hard Rock (short easy walk from the BR) Harrah's and others. The other way it leads to Island View, about a 45 minute drive from BR. BR and others are right on the Gulf and you can get a room overlooking the Gulf, very nice. Sometime in the spring they have "Cruisin' the Beach" where folks bring their vintage cars and parade the Boulevard. Folks bring a lawn chair and sit watching the cars. I used to always order the Crusin' the Beach Tee Shirt of the year for husband.
There is an area they say is really nice to visit, I forget the name, but a nice 'vintage' town area with nice shops etc. I vow to do that one next time. A supposedly wonderful restaurant, Mary Mahoneys or something like that across and down from BR. My pastor says he and his wife ate their on their honeymoon (60 years ago). We always have so many food comps at BR that it is tempting to use those in the in-house eateries, but again I vow to do a meal there some day. There is a Waffle House across the street. Biloxi is calm and laid back, very nice area. Try it if it works out for you. Last time at BR we ate in Salt & Ivy, their cafe but more than a cafe, and they had the best fried catfish I have ever eaten.
Candy