1. Need more info for the cutting off. Maybe any codes stored in ecm, recent maintenance performed, etc. Could be cross threaded filter but I would suspect it would have a leak.
Here is a picture of a bus I have. The filter is crooked but it runs fine.
99-3engine 2.png
2. See post #12 and #23
in this thread. #12 has a pic of a filter positioned like yours. #23 describes the wire that needs to be replaced.
3. Sounds like a split radiator. If facing radiator from front the left side is the radiator and the right is the air cooler for the turbo. You could pressure test to verify a coolant leak. I found it to be cheaper to buy new than repair.
4. If(when) you replace the radiator, completely flush engine and go with new coolant. I used Final Charge Global because I couldn't find any info as what to use for this yr model engine. A lot of good opinions from experience yes, but nothing from manufacturer. Use a coolant filter with no additives. Hastings WC8 is what I used.
5. Good luck. You can find info on the major components of the bus but I gave up on wiring from that year.
Use the search above to find a lot of the info you want.