Value as in not real high is correct. Don't take that as it not being a worthy car. For a driver it might be a good purchase. As you note, cheaper to get into than a Chevy.
Power Steering and Power brakes aren't real common on mid 50's cars of this type so there is that. The car will stop fine in normal traffic. Drum brakes work just fine except for when they get hot. In normal driving they generally don't have a problem. Disc brakes swaps aren't difficult or all that expensive though. A bracket and mostly off the shelf parts.
No, swapping in a 350 is not a bolt in job. Make sure the driveline is good. You can get Pontiac engines affordably but they aren't found as easy.
All depends on $$$$
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