Hi Herman,
I've had both. Way back when 356's were cheap I had 2 356C conv. The second one's engine was modded by some factory mech. friends in Weissach to about 145 hp as fun side project. Cost me 2 cases of beer and one case of wine.
, which was all I could afford as student.
But getting reliable 145 hp out of the 356's 1600 pushrod engine is pretty hard without Porsche factory resources. A VW type 1 or 4 engine is much easier to get to that power level.
I also had numerous 911's (71 S, 74 2.7L, 80 SC, 91 964).
From a handling standpoint the 356 is a VERY different beast from the 911. With regards to snap oversteer, the 911's (even the early ones) are docile compared to a 356 driven in anger. If you know what you are doing, they are more fun IMHO, but there will be a learning curve. See-sawing around tight corners with the tail hanging out at a crazy angle though is fun.
Also I saw you want to move to canada. With a 356 in cold climates you always need a passenger to do the ice-scraping on the inside of the windshield while driving. Believe me, I know.
Regards,
Klaus