What would you include in a Top 10/25 list of US coins under $250?

Some of the more obsolete types would fit your requirements I think. Some collectors unfamiliar with the series might not even know that 150+ year old coins are available in high grades for relatively little. Yes these series aren't heavily collected/promoted so I'm not sure if they would be a good investment, but they do offer a lot of bang for the collecting buck especially if one likes classic U.S coins.

I've always though that common date 2 cent pieces in low MS were awfully affordable. An 1866 BN in MS-63 is only $180 in Numismedia.

Some of the common year 3 cent nickels are cheap too for their age.
1866 in MS-63 is only listed at $175 in Numismedia.

Half cents have always been the redheaded stepchild when compared to Large Cents but you can get a nice 1851 BN in MS-61 for $240 or thereabouts according to the priceguides.

 

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^those are all great coins.

I just picked up an 1852 large cent for $132 in AU-58 condition. And from the pictures (which aren't great) it looks like a nice coin.

I'm also a fan of the odd denominations. Especially clashed nickel 3 cent pieces.