As far as the equipment bag:
I agreed with Bossman about the bag at first. I just emptied out my son's catcher's bag and loaded all my umpire gear into it and hauled it away. And I struggled to keep things organized and clean, and I had to employ a system of other bags to segregate and carry all of my accessories and undergarments.
Then, I sucked it up and bought the Diamond Wheeled Umpire's gear bag.
Good grief, you wheel the thing out to the SUV (Standard Umpire Vehicle), throw it in the back, and aside from your slacks and shirts, absolutely everything you need to umpire a game is in one bag! (I keep the pressed duds on hangers.) The big gear (plate shoes, leg guards, chest protector, two masks
and an HSM) is all situated in the bottom compartment. In the top section there are three main compartments, which hold two cap keepers with six caps and a travel kit on the left; a dozen compression shirts, two pairs of tights and a cup in the middle; knee, thigh, back and ankle braces, belts, socks and ball bags in the right section (I don't put my uniforms in it like the picture shows); and in a separate vented compartment: base shoes. The top flap has mesh pockets for your brush, wallet, indicators, stopwatch, sunglasses, etc. And it has several zippered pockets for your other supplies and accessories. It's awesome. Wilson makes a similar one, but, despite being a Wilson man, I went for the Diamond. And it takes a beating.
It helps you stay all managed and prepared and eliminates a great deal of the stress and anxiety about having everything you need when you're going to a game. It's not cheap ($120.00-$150.00), but it is easily the best investment in organization and peace of mind that I have made as an umpire.