As others have said, you will have to do a lot of trial and error to figure out what works for you.
What I like to carry is a glock 19, in a Comp-tac minautar (IWB) holster with an uncle mikes kydex belt.
Here is why I like it:
Glock 19- 100% reliable, easy to service, and for me (I'm 6'2 220) it is just small enough to conceal easily - it is just short enough that I can't feel it when I sit down. Also, it doesn't have a decocker or external safety to fiddle with when drawing the gun.
Whatever gun you decide to carry, the draw should be the same as the other guns you regularly practice with. For example, don't keep a glock in your nightstand, and carry a 1911 cocked and locked - you might forget to unlock it.
Comp-tac holster. Rigid plastic holsters are not comfortable. Leather holsters don't work in hot humid weather - they stretch and shift. Also, leather IWB holsters are very difficult to practice with since they close up when you draw and you have to stick your fingers in there to re-holster. The Comp-tac minautar is (for me) the best of both worlds. It has a big slab of leather against your body, but there are three sides of plastic to keep the holster rigid and in place.
For me an IWB holster on the strongside is the best bet. I can't open carry in Florida (and I probably wouldn't) so its IWB for me. A cross-draw almost requires you to sweep the guy to your left when you draw it, so practice is more difficult. Also, a cross-draw is more susceptible to being grabbed in a scuffle. The only situation where strongside carry is not great is while driving, since the seatbelt is usually right over top of the gun. I don't drive around bad neighborhoods much, so this is a tradeoff I can live with.
Kydex Belt - It doesn't much matter which belt you go with, so long as it doesn't stretch in the heat and humidity. Kydex liners are as rigid as they get, so I just started there and never left.