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Deacon, I am going to weigh in on your rifle choice, as I had a similar choice once.  My 1st CAS rifle was a Winchester '94 Trapper in .45.  What a horrible gun for this game.  Maybe better than a Big Boy?  But at the time, it was the worst.  Due to the design and the 9 round limit.  So my next gun was a Navy Arms stainless '92 in .45.  Stainless because I wanted to start shooting BP and thought you needed stainless (right now, I own zero stainless guns).  It was a huge step up from the '94, even though the action wasn't real smooth even after some work.  I did shoot BP in that one for a year or so, but then I got my 1st toggle rifle, a 44 Spcl 1866.  That was a straight wall case also, really no better for BP than the .45, but the action made it so much nicer to shoot that I never shot the '92 anymore and sold it whenever I got a '73 in .45.  Yes, the '66 needed more cleaning after shooting BP than a dash caliber, but it always made it through the matches, just needing a spritz of moose-milk or plain water when the carrier would get sticky.  This would usually be right after I finished a stage, never in the middle of a stage.  That '66 never had a short stroke, but I did the "poor man's" action job on it and it is quite smooth.  My concerns back then were not the functioning of the rifle, but that the bullets would have enough lube since I was relubing smokeless bullets with their tiny lube groove. Sometimes I would need to give the bore a swab mid-match.  BP subs would eliminate that, though.

So, I'm going to say go with the '66 in your choice, simply because it is more pleasant to shoot than a '92 IMO.  The fact that it will get dirty and need cleaning is just part of the game.  Most of my BP main match shooting now is .38's in a '73, even though I do have a '92 in 32-20 which needs less cleaning.

  WHAT ??

"Relative Newcomer??"  Newcomer??  Well, ok, I've only been play the game since 1990 or there about.  But the answer will take a couple of minutes -
1.) Sure.  Most of the time I'm showing a pair of .44 Navy Pattern SNUBBIE Pietta Cap Guns.  Sometimes I switch off ('cause I be lazy) to a Pair of 1860 Pietta conversions in .45, wid short barrels.  I switch to Suppositories for "Lazy" days.

2.) Nope.  Don't have "Wet Weather" guns.  I don't shoot in the rain any more.  Being wet is not in my lexicon of FUN.  I go home.

3.) I do switch up to .36/38 just for grins and giggles.

4.) No desire for any guns other than what I already have.  I switch between different 1860 Henry rifles.  They are ALL .45s but are of different barrel length.

5.) I don't consider shooting Black Powder (Black Powder is NOT Holy) to be a hassle. I just prefer APP.  Either Black or APP are actually easier to clean than that heathen, fad, smokeless stuff.

6.) Nope.  I don't shoot smokeless anymore.  I consider smokeless to be rather boring.  Black and APP are FUN.  Much more fun to shoot at targets you can't actually "see."

7.) My Shotguns are ALL Hammer Doubles.  Hammer guns are just much more "CowBoy" than internal hammer guns.  And more of a challenge.  I also shoot my shotguns with All Brass hulls.  Again, much funner than plastic.  I also anneal ALL of my .45 rifle rounds.  My .45s shoot as clean as any "dash" caliber and are easier to reload.  My 16 inch barrel Henry Trapper requires Cowboy 45 Special cases to load 10 and is a real hoot.  I also have an 18 1/2 inch Carbine and a 19 inch carbine, all of which are custom built.  Henry's are capitol FUN you betcha.

I also shoot Gunfighter.  My Cap Guns have to be every bit, if not more reliable than Suppository Shooters.  ALL my Cap Guns are dead reliable. 

Mako, no, the question is inane.  I don't make it habit of listing my guns on a public forum.   Who cares what others shoot?    It's often a matter of what a person can afford, likes, has available to them or appeals to their sense of history, or any number of subjective reasons.  As a matter of fact, I do shoot percussion pistols, 36 caliber ones to be not quite specific.  Been shooting one of them since before there was a Frontiersman category in SASS, back when all we used was a single pistol..., well, before there was a Frontier Cartridge category, in fact.  So I've shot in the rain with percussion pistols many, many times.  I shoot a 45 Colt rifle, which specific one is a matter of whim on any given day... I shoot a side-by-side shotgun, 12 gauge, and again, which specific model is often a mystery, even to me, (although my current choices are down by one, it being in the shop for repairs), so it's either a hammerless with 20" or 26" bbls, or maybe the 26" or 28" hammered. 

My answers in [brackets}
Do you have different choices for different matches? [I shoot my Uberti Millenium 1863 NMAs for "serious" matches and 10+ other pistols for the monthlies. I also shoot less than perfect home cast bullets at the monthlies]

Do you have wet weather guns? [yes. A pair of suppository shooters (pistols that load from the rear) called Uberti Hombres in .357 cal and a stainless Rossi '92]  Especially those who shoot loose powder pistolas. [I almost always shoot Frontiersman but have stooped to shooting suppositories due to the dearth of caps]

Do you shoot the same calibers all of the time, or switch them up for grins or just to not get stale? [ I shoot mostly 44s in the C&Bs but occasionally switch it up and shoot 36s]
 
If you had your choice, within reason, and money wasn't an issue what would you shoot?  I don't mean wishing for original 19th century versions of everything... [Maybe stainless 4 or 6 inch Uberti Remington NMAs and a Henry rifle]

If you shoot a substitute powder is it because of availability, local laws or you just like the way it works and eliminate the "hassle" of BP? [ I will shoot anything that smokes in the shotgun: BP, Pyrodex, APP, Black MZ, 777, etc. In the C&Bs only 3F BP. In the rifle (357mag) I have settled on 3f 777 after trying everything from Black Canyon (you old timers might remember that one as well as...), Black Mag3, Clear Shot, Clean Shot, APP, BLack MZ, Pyrodex, & BP. I would likely be shooting just BP in the Rossis if the Snakebite bullet would have fed reliably in my rifles. All of the subs shot more accurately with little fouling using the Lyman RNFB 158gr bullet which feeds very well. I cast, size and lube all my cartridge bullets with 50/50 deer tallow and beeswax.]
Do you ever shoot smokless at some matches? [NEVER!]