Hi metamod,
Good questions. Thanks! I’m trying to answer 
Challenge #1: You are right, DROP tokens have similarities to CDOs. I think such securitization structures are very important financial instruments to provide liquidity on scale. These structures are not the reason for the financial crisis of 2008. They were the tool that was used but not the trigger. The trigger was as usual too greedy bankers and fund managers, a financial system out of control, and very intransparent securitization structures. Junk investments got a triple-A rating because even the rating firms were only able to check the securitization structure but not the single assets. Tinlake helps here. It makes the securitization transparent. Every single asset in Tinlake is represented by an NFT. Every investor can check asset price (risk score) and performance in a daily updated NAV, which is completely novel. The Asset Originator providing the assets has to have skin in the came with investing in TIN (the junior tranch) and has to take first losses. Tinlake shows fully transparent on-chain what happens today hidden in a Bank in CeFi. You do not need to trust the bank anymore.
Additionally, we work on fully decentralized underwriting, which would further minimize the trust in the Asset Originator as the remaining “central” piece.
Challenge #2: I think Asset Originator and Investors enjoy the usual benefits of DeFi: trustless infrastructure, works 24/7, interest per second, immediate borrowing, investment, value transfer.
There will be more soon. The power of composability and interaction with other DeFi protocols will make investing easier and more secure. You will not need to invest in a single Tinlake pool anymore but invest in another DeFi protocol, which will manage your investments, leverage, and may insure it as it is already possible for crypto assets. Real-world assets represent a unique opportunity for crypto investors to diversify their portfolio to make it less dependent on BTC and the rest of the crypto market (which is usually not much different). I also think long-term DeFi will be both cheaper for borrowers and offering better returns for investors. The margin banks are making today will not completely be assimilated by decentralized service providers (Asset Originators, Underwriters, Issuers, …). It will be an order of magnitude more efficient and will in addition reward all participants if they contribute to this decentralized credit system.
I hope that makes sense for you. Keen to get your opinion. -Martin