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I have liked the Collingses and Northfields I've played but I certainly wouldn't buy one blind if I loved my current instrument.

I'd say the time to upgrade is when you:
1. Play an instrument and...

I own mandolins with both C and V profiles and don't have much of a preference. To me, action is the #1, 2 and 3 most important factors in playability.

Update: I cut/scraped the excess away with a knife. The nut is free now and my action is much better after fixing the bow and sanding the bridge down a little.

If it sounds great and plays great, why change anything?

Seems like a marketing buzzword to me.

I have a plastic ukulele that I have tuned to GDAE it's basically the same concept. Only $50 too.
ukulele:...

I think some of both is good - first play some open strings, single notes, open chords, and closed chords. Then play a fiddle tune to see what it sounds like in more context.

It'd be very cool if you could take a peek inside the factory, although I don't know if they'd let you do that.

Weber F styles come up for that price range pretty regularly as well, and they tend to have a pretty traditional sound.

It may be that there's much, much better options at the low end (i.e. <$500) for guitars than mandolins.
$200 can get you a pretty decent Yamaha guitar, but the lowest end of mandolins that seems to...

It's hard to get the difference across in words. They sound different, there's not one better or worse. Here's a comparison of two Ellis A-styles with F or oval holes; it should give you an idea of...

Sonny has a few As on the classifieds for $1050 and a 3 point for $1300.
I also have one of his Fs and it's excellent.

https://www.ebay.com/itm/314654838959?mkcid=16&mkevt=1&mkrid=711-127632-2357-0&ssspo=mssjzDwLS8y&sssrc=2047675&ssuid=oi0Mk8-cTK6&widget_ver=artemis&media=COPY

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These two need to release a duo album!

Seconded on trying everything out at Fiddler's Green and letting your ears make your decision for you. It's the only way you can be 100% sure you'll be happy with what you get.

Yeah, the old Flatirons really have gotten pricey. I had mostly given up on finding one at a reasonable price until one popped up in my local music store earlier this year for $400.
The only...

I have similar feelings to JeffD. My travel/camping mando (not sure I'd call it a 'beater') is my Flatiron flat top. Sounds really nice, loud enough to take to jams, it was already pretty worn when...

I'd go for the Kentucky if it's in good shape.

This Hercules stand is great:
https://www.sweetwater.com/store/detail/UKS100B--hercules-stands-uks100b-auto-grip-ukulele-stand

Or a (clean) piece of sponge!

These Goodwill auctions often go for above market value. If you're looking for actual good deals, auctions on Ebay sometimes go for significantly cheaper than market, you just have to be patient and...

Sure, maybe I worded that poorly. I wouldn't personally put a $200 tailpiece on my $500 mandolin. Other people can do what they want.

I'm sure James tailpieces are very nice but I'm not sure it'd be worth putting a $200 tailpiece on a $500 mandolin.

You could use pretty much any strings on it, gauges are mostly a matter of personal preference. I'd experiment with a few if I was you.

Grab 3 picker friends, hop in a car together, and rent a cabin in the mountains for a week!