[size=12]Well, here's what I'd say, anyway...
First, I can't help you a whole lot on the Wagner, since I'm only really collecting Griswold. (I do own three or four Wagner pieces, but don't tell anyone.) But that's a pretty common style of Wagner. The red book (The Book of Wagner and Griswold by Smith and Wafford) says 1935-1959. I can't quote a current value, but they're everywhere, and Wagner usually doesn't sell as high as Griswold, so I would guess that it's not worth a lot.
The square waffle iron is a later style without leveling pins and without handedness of the two paddles/irons themselves. It looks to me to be a low bailed base. I have the same exact thing, and I once asked on this forum if the low base was much more rare than the high for square waffle irons. I think that the expert answer was that it might be a tad more rare, but not much. I'm having a hard time finding any pictures of the later style of waffle iron in the catalogue files and reprints at my disposal, but the Blue book (The Book of Griswold and Wagner, by the same authors as above) shows a later style and dates it to 1923-1930. All I can tell you is that by Catalogue 55, which dates to some time in the mid-thirties, I think, there was an easy-reference chart for ordering bases to correspond to older or newer style waffle irons with or without leveling pins, so both styles must have existed by the mid-thirties, anyway. Your coil handles on the square waffle iron are the thicker and heavier wire, but I don't know when they made that switch, either.
The round size 9 waffle iron would be a little easier to quote a date on if I could see the handles. If they're wooden, then it might be a touch older than the date I'm giving, since I think that they phased the wood handles out in favor of the coil handles. But... your round iron doesn't have a Griswold logo on the irons, which makes it a little older than the ones that do. The picture in a catalogue doesn't always correspond exactly to what they would have shipped on that date, but in Catalogue 47, dating to about 1918, they show a no-logo side-handle iron with coil handles, pretty much like what you've shown. In Catalogue 45, dating to about 1915, I think, they showed wooden handles. By Catalogue 49, from 1920, they were showing irons with the logo only. So I'd say that that iron dates sometime between 1915 and 1920, from what I can see.
Value? Well, I'm not the best to say, since I haven't been to an auction that recently that had many waffle irons at it, and I'm not active on e-bay. If I wanted to sell my 161/161/162 square WI, I wouldn't price it below $150, and the blue book suggests that they might go for more than that, although I don't know if they really do. That round No. 9 is pretty common, though... I've seen irons like that go for giveaway prices as low as $15, and I've seen them break $100. A 9 isn't really rare, but it's less common than an 8 and more common than a 7, I'd say. Condition is always key; any cracks or chips or serious pitting are going to put a major crater in the price tag, too.
Hope that helps.[/size]