Checking a large box?
 

I check a bag about once every 300 flights lol. For Xmas, I think it will just be easier/cheaper/safer to try and check an xmas gift than ship it.

It as a 49" ultra wide gaming monitor. The box is about the same size as a set of golf clubs so there should be an issue..... right? meaning, they will allow me too? I know the risks of damage etc but UPS ground will handle the box many more times across the country than the baggage handlers will between Houston and Palm Springs!

Yes, you should be able to check it (but calculate the box's total dimensions to determine whether "oversize" baggage charges will apply).

Be aware that some airlines exclude liability for electronic and/or fragile items which are checked.

I once asked for them to put the fragile sticker on a bag before, and it seemed like the handlers were indeed careful with it. I unexpectedly had to check some delicate items and only had a soft (weekender type) bag, but everything came out fine.

Total dimension rules still applies, 62 inches and not more than 115 inches (sports items have exemptions)

Best left in manufacture's packaging as it was designed for shipping.

UA will not cover damage for displays (or computers)