If you have a squeeze chute with a palpation cage attached to it, use this as a means to do your AI'ing. Some barns are set up so that each cow is in a stanchion or head-catch lined up beside one another. This is very convenient for the AI tech who has to AI over 50 cows in one day!
If doing AI outside, it is best to do it on sunny warm days, not when the weather is rainy or windy or even stormy. If you have a facility that is set up inside a shed or barn, so much the better!