Throw and raise errors in cli for functions at key points - like connections, uploads, file reads/writes, etc

[aaronlippold]

trafficstars

[Amndeep7]

To this end, might be useful to have some sorta 'base-output' class that'll handle this io to as high a degree as possible.

Anyways a concern with file writes is hitting maximum file path/lengths so that base output class could test if it's possible to create the file and then throw an error if it's not possible to create a file at all or spit out a warning and then crop the filename output if we're hitting the max length, etc.