Why do I prefer R2R over Chip based DAC's?

You need to save up for a Wadax. That is the only chip-based DAC that sounds any good, and probably the only one you would prefer over R2R ones . 😉😁

Atlantis

I thought all DACs are chip-based. Are there ones with discreet circuitry like separate transistor/diode components? What is R2R DAC after all?

The DAC it have the Topping D70 Pro OCTO uses a series of 8 Cirrus Logic chips (CS43198), offering a robust 8-core driver setup.

The amp is the Schiit Midgard. It is a fully discreet design. The first of it's kind for Schiit. 

You can read about it

https://www.schiit.com/products/midgard

There are three questions in your post. Why do I prefer R2R over chip based DACs? Am I not spending enough money? What should be my next upgrade?

Not to be rude, but your post is confusing.

I really think only you can decide what you like or how much money you are willing to spend?

I much prefer fpga based dacs. Numerous reasons: sound great, software updatable, more easily handle the hires or dsd files.