What is this and how much is it going to hurt $$

We can't jump to repairs until we finish diagnosis... It's fairly normal for early gen3 to loose coolant at this age and you can sometimes go years before needing to replace the headgasket and cleaning the EGR to resolve it.

But the oil leak issue needs to be identified and quantified as major or minor like you explained with coolant before we can address the concern. So far it looks to be minor...

As in clean up the mess it made in engine compartment and do regular inspections of where the leak is coming from and how much oil is being lost. Once you post that info we'll have lots of links to share about how to do the repair.

 

During your cleaning you can partially appease your annoyance by slightly tightening any fastener you can access....

 

The timing chain tensioner or oil pressure switch have been reported in addition to the timing chain cover relative to passenger side oil leaks.

Somewhat difficult to see although clean it and put on a lift. Remove the undercover and front passenger side wheel and access panel to help view the area.

 

Like the guy above said it's usually not the timing cover leaking most of the time it's the oil pressure switch I would say the timing chain tensioner could do this also It's over there in the same area on most of my Gen 3's I put in a new oil pressure switch I use my pressure washer and clean that mess up and it stays silver eat off clean for many years then the next time it happens it's that same switch again I rarely seen the timing cover per se leaking in any of my Toyota chain engines all the way back to 22R that was an engine.

 

The seal in the top where it turns from metal to plastic for the tang to stick out for the wire to slide on etc that seal blows out oil starts coming out of the very end and then it just becomes a mess The timing chain guide can also do that so there's two things right there on the side of that cover and that can be suspect way before the form and place gasket job FIPG is what's used on the cover Gray I believe

 

The slowly dropping coolant may be another can-of-worms; at 135K you're getting into the head gasket danger zone. Saying you've done just by-the-book maintenance, presumably you haven't cleaned the EGR system, including the EGR passages of the intake manifold? That should be done very, very soon (see top two links in my signature, on a phone turn it landscale to signature), but first things first, any rattle/shake during cold starts?

 

have EGR Cleaned ASAP!!!!! For sure.