Multiple questions on weather proofing connections, air gap, mounting, protection for garage rack UPS and PSU

[BlueToast 0]

1. I am looking for suggestions on weather proofing the connection of an RJ59 Siamese cable to an HD-TVI camera that is mounted outdoors. Specifically, I am wanting to know how you would go about doing this and what hardware you would use. Reliability through changing seasons and weather is definitely a must (I have learned from experience, aww, camera video feeds keep going out).
    
2. Do you have any recommendations on how to get the video feed of multiple HD-TVI cameras on one building over an air gap to the other building? The distance between the buildings is less than 300 feet and there is pavement that prevents us from doing underground cabling.
    
3. In further extension of question #2, the building in particular is a workshop garage for vehicle repairs. The need is to install a wall rack with CCTV power supply and UPS battery backup. What is the best way to do this factoring in cold winters (below freezing) and hot summers (upwards of 38 Celsius / 100 Fahrenheit), particularly in protecting the equipment from overheating and the elements?
    
4. In general, how do you recommend installing [bullet] cameras outdoors? In particular, do you install bullet cameras directly to a surface on the building, or do you install the bullet camera to some sort of weather proof junction box? What equipment do you use? I am hoping for some photos of examples and/or product links that I can order online.
    
5. What is an ideal mounting height for outdoor cameras where a ladder is required to tamper with the camera but not so high that faces cannot be identified?
    
6. If you are running a cable through a sheet metal wall, what do you use to prevent the drilled hole from cutting the cable and how do you weather seal the hole after running the cable through? What equipment do you use?