1. Chile was much smaller, didn't fell apart tearing supply chains in the process, and had only 1 major export good - copper (the price of copper was relatively high at this time, too). Not really applicable.
2. China didn't wait until their economy (and the country itself) collapsed. Chinese model could've worked for USSR in the late 70s, but not in the late 80s. Soviet leadership preferred half-measures over structural reforms till the very end. Plus, the presence of HK really helped China to build its own financial system.
3. Other Eastern bloc countries had more consumer-oriented industry than USSR, were more permissive towards market mechanisms and didn't have massively oversized military-industrial complex. Attempts to convert USSR military factories to civilian in the 80s resulted in meme-worthy products like titanium shovels and inconel stoves and couldn't make factories profitable.
4. And in Russia, hardcore commies weren't allowed to return to power at the cost of subverting democratic procedures. In short-term, it seemed like a good decision, but long-term consequences were catastrophic.
5. Tons of Soviet assets could not be sold or generate interest. Also, if Russia had declared default on Soviet debts, it would be much harder to attract foreign capital. Trying to distribute the debt between successor states would have led to massive shitshow.
6. At ~$20 a barrel the oil wasn't a life-saver in the 90s. And as far as I remember, Western oil companies were paid and/or got concessions, standard market cooperation.
7. How can kleptocrats create safeguards against kleptocracy? It comes down to luck and access to resources. Out of 15 USSR successor states, only 7 are democratic, 2-3 are hybrid regimes and other are autocracies.
