Bitcoin is all the hype, but the blockchain has flaws, in that it isn't as anonymous as one would hope for — you can track past transactions. Is Bitcoin the way to go, or will it falter under wide use / become easily trackable once NSA and the likes adapt their systems to doing exactly that? Are there feasible cryptocurrencies that have the upsides of Bitcoin (such as a mathematical limit to their amount) but are fully anonymous in transactions?
There are a number of properly anonymous cryptocurrencies now. Dash (formerly Darkcoin) and Monero are current market leaders. Zerocoin is a notable new contender as it uses zero-knowledge proofs which are as good as you can get on anonymity. Bitcoin on the other hand would require dramatic changes which are very unlikely to receive support from the institutions involved with it.
So I have some questions: Is getting into dealing with crypto currency worthwhile already?
Only if you're a fan of economics and programming. It's still very much in the experimental phase of technological maturity.
Rumors of Bitcoin showing cracks are popping up and also there are quite a few alternatives out there. And does Bitcoin own the market or is it still flexible enough for an technology upgrade?
There's currently a holy war going on between different groups of Bitcoin developers on how to upgrade network protocol, which is sorely needed given Bitcoin's dinosaur status in the field. Looking at that there's definitely not much flexibility. There's also not much of a market to own yet, so despite its network effects, Bitcoin could easily be dethroned by a cryptocurrency with actual momentum in becoming useful beyond largely experimental purposes.
What digital currency has the technical and mind-share potential to supersede bitcoin? What do the economists and digi-currency nerds here have to contribute on that?
Ethereum has by far the strongest development community at the moment. It's also designed to maximize flexibility in what it can be used for, giving it abilities to adopt new features as needed without requiring agreement among those using it (pick and choose which features you want to use for all but the most fundamental).
What are your experiences with handling and holding cryptocurrency?
Dodged a couple exchange collapses, scary stuff. Keeping wallets local, encrypted, and with multiple backups is a considerably safer experience and doesn't require too much involvement. Getting holdings in the first place is also a hassle.