I have a couple big issues with Waves from an investing perspective:

1. Waves is bland. The platform does nothing new and the things it does do it doesn't do exceptionally. From a technical perspective it's decidedly average. There's no secret sauce, nothing new, no genius developers. Sure, you have all the compelling crypto applications (crowdfunding, DEX, app tokens), but so does every other platform (Ethereum, NXT, Bitshares, etc...)

2. Standard PoS is not secure. Lazy choice.

3. Sasha's previous project coinomat was horribly unsuccessful.  

4. WAVES has no fundamental value other than securing the network so there isn't even necessarily a correlation between the success of the platform and success of the token. It isn't gas and unlike other PoS platforms it's not required to make transactions. Fees can be payed in other currencies. This means there isn't even really speculative demand for the platform token.

5. It's current valuation is pretty high with regards to platforms that do similar things.

It does have a few positives:

1. Huge amount of money raised.
2. Basically still at ICO price so there's appreciation potential.
3. Being actively developed.
4. Has at least one serious dapp (Incent) developing on it.
5. Should be listed on Polo at some point.

Ultimately, there are far more compelling projects to invest in.