Yes. When you put things in the crate, it fills up a white bar at the bottom of the crate UI. Once the white bar is full, so is the crate.
Also make sure sure to take attachments off any weapons or they'll disappear over restart/ log out
Yeah, in that case I'd say they should try fishing or excavating or maybe mining. Mainly things where you have to collect a lot.
They patched this somewhat recently
Escort them to the court house in any main city. You can see where court houses are marked on the map in green text. Once you get there just scroll wheel on them and select send to jail.
First module is rumored to be released by the end of March. There's going to be 3 modules before the Closed Beta which is suppossed to be in 2018.
More on the modules: http://identityrpg.com/info/modules/
Not saying I fully support it, but if it was done, it should be like the drill in Payday 2 where it breaks down occasionally so you have to restart it and not just AFK the whole time. Also cost a lot more than $150k and cost a lot to just pull out