If your Non-0 multi (1 year) is about to run out and you cross land bridge to get a final 90 days, can you get a re-entry on that 90 day stamp ? (1 year + 90)

Yes, be aware that when you enter on the re-entry you will get same expire date as your original 90-days entry, you will not gain any days will out of the country.

If you have crossed a land bridge on a multi 3 times do they count that against the 2 times rule??

 

2 minutes ago, buckeye said:

If you have crossed a land bridge on a multi 3 times do they count that against the 2 times rule??

 

No

The 2 entry rule at  land border crossings is only for visa exempt entries.