Just what I know...
Both are very Jap chopper in character...
... but different in technology...
The 800 is water cooled, more revvy less torque... feels like a Honda... refined, but lacking character... it is complex... 2 PIA air filters... hard to reach battery... not fun to work on...
The 1400, I know only from reputation... but it is powerful... by several degrees of more...
I thought about the 1400 myself... but weighting the pluses and minuses... I can't justify the added weight, cost, and complexity,... over my Savage...
Either is a magnitude much more than just a step from a Savage... the 800 in complexity, the 1400 in power...
JMHO... and I've never even ridden a 1400...
I'd take a Sportster over an Intruder 800... same power, better resale, better quality,and simpler...
I'd take the 1400 over a bigger Harley...
Honestly,... I'd take Triumph over any of them...
...