I need brown shoes and really like a lot of different kinds. How do I decide between the various types rather than getting tons of shoes all at once?

Trying to get new shoes, specifically brown ones (currently I only have a pair of navy sneakers and light blue canvas boat shoes). I've spent a lot of time reading the shoe guide, various inspo albums, as well as trying on shoes in stores. Problem is I've come to really really like about 10 different types of shoes at this point, but figure I probably shouldn't quintuple my shoe collection size overnight.

I figure I should have one pair of shoes (probably boots) for rainy days (doesn't snow or anything here), and then maybe a more casual/light pair. I also don't really have a good dress shoe so I'm hoping to get something that I could wear with a grey suit but also jeans, if possible.

Also my current pants (all skinny) selection is burgundy, olive, dark denim, grey, and black, so I'd like shoes that work with as much of those as possible. I'm like average height/build (5'9", 160lbs). Work is very casual so I pretty much wear the same clothes to work and offtime (OCBD + chinos + wingtips is about the most dressed up I could do for work, though that'd be fine). Budget's not super tight but I would only spend more money on something if I saw a good reason for it.

Now, shoes I'm torn between: I really like CDBs of course, though less so in beeswax. What do you guys think of the mustard or oakwood colors? Are these colors less versatile? I have trouble knowing how different shades of brown are different in terms of matching lol. But I figure those 2 shades would still go with all my pants except probably the black? Also maybe if I got the bushacres this could be my "rain" shoe?

For the dress shoe, I've really started liking wingtips, in walnut color or so. Basically the AE McAllister, though I'm a little scared of wearing wingtips too so I'd probably get a cheaper brand at first. I'm not sure if these would go with anything in my current wardrobe but jeans and grey chinos (and hopefully grey suit). The part of me that's scared of wingtips wants to just get a plainer type of dress shoe (though maybe then I couldn't wear it with jeans as easily).

OK then for a more rain-appropriate shoe I like red wings a lot (both IRs and classic mocs, I think I'd lean towards mocs a bit) or wolverine 1ks. Honestly I like all 3 of those quite a bit but have no intuition why/when one of these would be better than the other. I've also really started liking chelsea boots, probably in dark brown (could these also be okay for rain?).

I also really like tan suede buckinghams, though I'm not sure how they fit in here (similar-ish to CDBs?).

Anyway the hardest part for me is knowing why I'd get one pair/color vs the other—haven't been able to figure this out from the shoe guides. Like when would you wear a chelsea boot over desert boots? What styles do each suit the best?

And yeah I really like all of these shoes but am having a hard time deciding which are most important to get rather than just buying all of them lol. I suppose it's best to start with the most versatile first (not sure which those would be).

Thanks guys! I'm really loving this sub so far.