Just so that you know, all the major editors support shifting the background imagery by letting you drag it with the mouse to what you think is correct (road from gps traces, etc).

I'm not sure what the tag is, but there is a tag indicating that a building no longer exists. This would allow you to map it and mark it as no longer existing, which would keep tracers from re-adding it later on thinking it had just been missed in the surveys.

-Buck

It's still definitely worth knowing how to use JOSM though. You should check out the list of plugins for it as well (in the preferences menu). One of my favorites is the add buildings plugin. I have added hundred of building with it very easily, and it also lets you make nice orthogonal squares for things like parking lots, fields, landuse, etc.

Regarding the area that has cloudcover, you may want to consider connecting them up with just a staright segment which forms its own way. Tag it like you are tagging the rest of the railroad and just include a 'fixme' stating that the location is not correct but the railway still is there somewhere.

Although I don't think anyone is doing "routing" on the rail networks like they are with roads/footways, someone may want to do some analysis of rail connectivity and adding in that segment would help with things of that sort (including your question of how much rail is therein fiji).

Anyway, glad to see other people working on stuff like this. It is this rich variety of data that makes OSM so useful. Keep up the good work.

If you have information about POI's that you are unsure how to enter you could always just create a point with a fixme tag on it containing a description of what it is. For example you could do something like:

fixme = Joe's Pawn Shop, 922 3rd street.

and then just list any information you gathered/know about it like that. There are may tools available that help people locate nodes with fixme tagged on them and if you entered them this way they could easily be filled in later with the appropriate tagging scheme by someone else. Good luck with your ground surveying.

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Haven't done much at all with Montana, but I do a fair bit of work in western North Dakota. I have done a bit of the TIGER cleanup as you describe as well as classifying the gravel roads and such properly. Good to see there are some other midwesterners on here. I'm going to friend you so I can find you in the future if I think of something we can work on together. :)

-Buck