My friend is a software engineer and quite tech savvy so I dont factor human error.
That's a mistake.
Just because he is a software engineer, this does not automatically mean that he actually knows how to use bitcoin.
You can't assume that someone is familiar with BTC just because his profession is IT-related.
Its been two days and I see no record of the coins. What do I do? He used an older address but I know all addresses generated are linked and new ones are just for privacy.
If old addresses stay valid and the transaction went through successfully (is it confirmed already? Check the transaction id.), then you need to contact the coinbase support.
The mempool is relatively clogged right now. Not that extreme that a 1 sat/vB transaction shouldn't be confirmed by now, but you'll never know. Maybe it didn't get broadcasted properly?
Definitely check the Transaction ID on a block explorer (or post it here).
Did both transactions have the same
recipient address?