K, clearly I'm not getting anywhere here. I'll figure out. No worries.
That's because you don't give the needed information. Without complete and unambiguous information on what you're trying to do, you can't get anywhere. Please remember that we have NO CLUE of what you want to do until YOU TELL ABOUT IT.
If you feel you're not getting anywhere it's because you don't give the information needed to work with. No photos, no proposed schematics, no details on the components used, no word on the purpose of the project, not even on WHY there has to be such a distance.
I can get 30 feet, getting closer is just impractical, not impossible, but I don't feel like grabbing a ladder everytime I have to go up
This also doesn't make sense. Why would you put either the Arduino (or the buttons - which makes even less sense as somehow you will want to be able to operate them) in such a hard to reach place?
What is it what you're actually trying to accomplish?
It's mechanical switches and indicator lightsAnd that's why you're getting all those questions.
Sorry if I'm a little vague, I'm a PLC and hmi guy, this is a new area for me
What kind of indicator lights (LED, light bulb, strobe, search light)? How much power do they need?
What kind of switches? Push button or on/off switch or something different entirely?