So I ordered a new desktop, should be here Tuesday.

Old computer is running windows 10, new computer will be running same.

What is the most painless way to transfer all of my files, settings, programs etc??

Clone the hard drives? Backup software?

Depending where you purchased it, Have them do it. Like Geek squad

3 minutes ago, Brisco said:

What is the most painless way to transfer all of my files, settings, programs etc??

Clone the hard drives? Backup software?

Get one of these. Set up an automatic backup so it copies your files everyday.

https://www.amazon.com/Passport-Portable-External-Drive-WDBYNN0010BBL-WESN/dp/B01LQQHIEC/ref=pd_lpo_vtph_147_tr_t_2?_encoding=UTF8&psc=1&refRID=C340P5Q7SQBZ090RPZ4X

Programs will have to be reinstalled on the new computer, data files can be copied over.

There is no easy way to do this, you cannot clone a hard drive and expect it to function utilizing completely different hardware, You will have a driver nightmare on your hands.

All settings will have to be manually changed, and all programs manually installed. 

The only thing you can do is transfer files. That can be done by either backing them up like sniper suggested, or finding a P2P sharing program through a network connection(far more complicated if you dont know computers well). 

21 hours ago, Bklynracer said:

Depending where you purchased it, Have them do it. Like Geek squad

I had geek squad do that once and they losy all my info, erased computer and disk was blank. WTF and still charged me.