You guys are just dying for my input.
Everything decent has been already said. Stay away from big name brands like Boss. Cheap quality, over-manufactured and over-priced.
No black. Keep it simple. Navy or grey suit. Blue shirt. Blue grenadine tie.
If you want to spend around $1000, Samuelsohn (Canadian) is your best bet. Full canvas, good wools, and good craftmanship. I have a suit, and two sports coats from Samuelsohn, and I love them.
Big lad like yourself should tend towards something more relaxed, do not attempt slim fit at all. Get trousers that sit higher, rather than lower. Consider braces or suspenders. They allow for a looser fit around your middle, and won't emphasize your stomach. Similarly, tapered trousers will emphasize your stomach.
Pay attention to fit over price and construction. You want function,but you want to look decent. Why spend $500 to look like someone who spent $500? Get that sucker to a tailor, and drop another $100 on getting those sleeve lengths adjusted etc...
Also, for buying options, here is your best suit for around $500.
http://us.suitsupply.com/en_CA/suits...pring%2FSummer