No offense, but please get more into adb and all the tools needed for reflashing.
Making things idiot proof is useless in my opinion. If you have no idea how to use adb, why upgrade anyway? Chances are you won't understand most custom upgrades/tweaks anyway..
All releases by HTC will be idiot proof, no doubt about it, but installing a custom rom takes skill, knowledge and patience.
In general, an idiot posseses none of the above.
Second, there are no custom roms available for the Hero.
If you want to install custom roms in the future, take some time to understand things. Spoonfeeding this info won't learn you anything.