Any power adder can exceed the capacity of the stock block if pushed all that hard... and that is with the stock 302 stroke.
Stroking puts extra strain on everything, making the assembly able to handle LESS power. If using a power adder, I'd stick with the stock 3.00" stroke. You'll still be able to use the stock crank and rods as well, as long as the machining is good and ARP Wavelock rod bolts are used.
As for which is easier... blowers are easy enough on EFI cars, but carbed cars are a pain to get right with a blower. I'd go the the nitrous route with a carb. It's simple, easy, and when it isn't in use, the drivability is unaffected. Carbs and blowers are a pain.
By the way, the B&M 144 is no longer in production. Holley took over the B&M/Weiand blowers and now only offers the 174ci version. It's good for around 14psi or so.
Good Luck!