Can you cut baseboard

yes you can, some of the thicker baseboards, it is better to use an electric miter saw

Craftsman cmht20800 and stanley 20-800 look like identical tools, is there any difference?

Don't own the Craftsman but they sure appear identical except for color scheme. Makes sense since Stanley Black & Decker owns the Craftsman brand.

Can this saw cut 5 1/4 baseboard and if so lying flat or standing?

The specs say 4 1/2" max cutting height and that is what I measured. If you go taller than that then the top ring of the blade guide will off the rod so it would be tricky. Max cutting width is 6 1/2" at 90 deg.

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Specifications

Brand	STANLEY
Color	Silver, Black
Blade Material	High Speed Steel
Surface Recommendation	Wood
Power Source	Manual
Special Feature	Quick cam clamp
Included Components	Saw with induction hardened teeth
Warranty Type	limited lifetime warranty
Item Weight	7.2 Pounds
Blade Shape	Rectangular
Handle Material	Metal
UPC	076174208009
Manufacturer	Stanley Consumer Tools
Part Number	20-800
Item Weight	7.22 pounds
Product Dimensions	48 x 8.6 x 4.6 inches
Item model number	20-800
Is Discontinued By Manufacturer	No
Size	‎48 x 8.6 x 4.6 Inches
Item Package Quantity	2
Special Features	Quick cam clamp
Batteries Included?	No
Batteries Required?	No

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