druff,
i'm going to do you a solid here. i've been involved in watches for over 20 years. i also use to work at breitling. you can call me a motherfkn expert on the subject.
i am going to recommend a few watches that you would be proud to wear next to your wsop bracelet. even if you wear 3xl sweats and other clothes off of the kohls clearance rack at the poker table. i'm not going to critique your polo shirt or other fashion or non fashion wardrobe choices.
i can only generalize on your lifestyle and physical size. i take it you're 6'4 and around 230? not as big in our current time as in the 80's / 90's but you're still a very big dude. this will allow you to pick larger watches and give you more choices that you can pull off. it wasn't that long ago the being 5'8 was average sized.
i take it from all the years in the forums and remember threads you want to lose weight that you don't lead an active lifestyle. what i mean by that is you don't really do that much running, biking or swimming for exercise. also,..from your frugal nature i don't think you want to spend 5-10k on a watch that you don't feel defines you or is necessary. (yes i know you can afford it it you wanted it) i can relate to some of this. paying that much for a watch will make you worry. worry about something happening to it, banging it, etc, etc. being a slave to your watches isn't good.
now that we have that out of the way we're going to focus on pricing. from what i gather i think you might be comfortable in the $500-1000 range. if you're not, then we really have to look at vintage watches from $200 -500. either of these price points are excellent and the watches i recommend will not lose any or much value should you decide to sell them. i always recommend vintage and pre-owned. but you can still find good deals on an acceptable watch new. if this is about making money always buy vintage. (but i don't think money is a prevailing factor here.) however, i don't recommend going any lower.
another consideration and very important factor is comfort on the wrist. this is very important as we age. even if you like a certain watch, if it's a brick on your wrist you just may fall out of favor from it. larger watches naturally are heavier. put them on a nice bracelet with and it becomes even heavier. if you were to sport it with a nato or leather strap it will be less weight. but i can't say it will be any more/less comfortable either way.
now it comes to watch taste. people are all over the place when it comes to this. just because your conservative doesn't mean you don't want any style or bling to you're timepiece. it could be but i don't know. i'm personally not a fan of polished stainless steel. most/some love it. it's dressier and on quite a few of the new watches. it's pretty much unavoidable to some extent with mainstream brands and it's not necessarily bling either. it also seems like rolex and other jewelry type watches will have both brushed an polished surfaces. on the flip side of this there is pvd and bead blasted finishes. i won't really suggest those for you. maybe a pvd. titanium is definitely in the ballpark.
knowing what i know i will present several options. i will mainly focus on 40-42mm in size. you can always go 38mm but it might look like a stamp on your wrist as you're big guy. i will try to not recommend 43-45mm unless you really like that size. (you prolly can pull it off as well. so maybe)) smaller watches do mean less weight and more comfort though.
i guess the guidlines i wrote above can apply to many in here.