Firstly, Welcome to the forum!

I how wrinkled they get kind of depends on how good a job you do of making sure everything is nice and smooth when you sit down. Most of the time all but the worst creases will shake out after you walk around a little bit. You shouldn't need to press or clean the kilt that often if you look after it a little, but be aware that if you need to clean a wool kilt drycleaning and a lot of pressing is in order.

Honestly I think if I was in your place I would look at a PV (not acylic) kilt like a USA Kilts Semi-Trad. The PV is a good wool analog, but cooler in hot climates and easier to care for, it can be machine washed, hang dried and ready to wear the next day.

http://www.usakilts.com/index.php/ki...onal-kilt.html

A kilt belt is not really "needed" since as you note the kilt has it's own straps and buckles, but it is a traditional part of the outfit and many folks feel they look incomplete without one. Most kilt belts are around 2 1/4 inches wide. Most kilts come with two 'belt loops' at the rear, there is some disagreement here about whether they are for both the belt and sporran strap or just the strap, or neither!