Big or Small ?

Trying to make a decision on what to do to the Tempermental Demon.

Right now I figure the 340 is going to need to be torn down and gone thru to figure out the smoking issue, Probably just a rehone and new rings. I don't think these ones ever seated correctly.

Second Choice is to tear down the 440. and go thru that.
Has been run over 14 years in 4 or more cars, so I'm not sure how much machine work would be involved.

I have all the parts to put the 440 in so that's not an issue. It's also already been in the car before, so it's only a weekend swap over to get it going again.

The small block will also require me to rebuild the tranny.
The BB trany will need to be opened up and inspected, but works well.

Both engines have powered a car to the 12.60 at 102-105 mph. which for the basically stock 440 isn't to bad. '68 440 with '67 closed chamber heads, 750cfm Holley and a 509 MP hydraulic cam.

Financially this is going to be a tight budget, but I do want to be able to run this thing more than twice a year, and not have to be screwing with it all the time just to make it run halfway decently.

Input is what I'm looking for. Bring it on !
Where do I go from here?