I have a unique situation that I am trying to fix regarding booting - any help appreciated

Hello, I work in a system development environment where we have many isolated networks that each rely on a single switch, and are not interconnected to one another or to a larger network. All of these networks are spread out across the world and we have to send technicians to do an update on the network and the system each year. These are not network technicians, so I am trying to make it as easy as possible for them to do. If I can totally automate it, I would eliminate a lot of the issues that can arise from someone who doesnt understand networking playing with boot variables and .cfg files.

I am trying to find a better way to update the IOS and config files on these networks. At its current state, the switch gets updated using a fat16 memory card. The new IOS and config reside on that card, and I have written a text file of paste-able commands for the field support reps to use once they are in enabled mode. Once pasted, the switch will push out the old flash, reassign a new boot variable, and install and assign the new config file before reloading to process the boot variable update.

The biggest issue that I am having is that these cards, and really any usb flash that I use, is that they're really finicky. The switches have all sorts of intermittent problems reading these, which leads to FSRs in the field at the "SWITCH:" prompt, where they are lost and in an opposite time zone.

What I want to do: I want to install a tftp server in the network, point the switch to that server, and have the FSR put the new files into the tftp server and reload the switch. Seems easy peasy.

THE PROBLEM: These networks are actually a contained system. A simulator for pilots to train on. And the whole thing is powered down in some locations each day. The issue that I think will happen is that when the system is turned back on, the switch will boot faster than the rest of the system, and it will not have a boot file to read from because the tftp server will not be online yet.

Any insight on how to get around this would be amazing! maybe in the config file, I can set commands to copy over the tftp boot variable into flash and then reset the boot variable to the static entry? what would be the best way to go about that?

thank you!