Am I just too paranoid?
Yes. Due to malleability invalid scriptSig are re-encodable as valid for any plausible signature type. This was explicitly considered and it's why BIP62 didn't impose changes on pubkey encoding requirements (e.g. requiring pubkeys be valid, or compressed), since whatever scriptPubKeys there are are set in stone. Height restricting strictder would completely undermine the motivation of the change, since consensus could be broken by anything spending an old coin.
One case that isn't covered is if you authored a chain of private-key-destroyed timelocked transactions using invalid encodings. You can fix-up the signature in the first transaction, but doing so changes its txid and thus invalidates its dependents. Of course, if you did this you were already likely to get burned even absent any further change: anyone in the network could mutate your transaction (and with the invalid encoding, all the network would already ignore it and take the mutant instead) and invalidate the child equally well. There already appear to be some parties that mutate any invalid encodings they observe to valid ones.
In general, I think long term timelocks like this are suicidally ill advised... but indeed, I do consider it important to not soft-fork out the ability to spend old coins, even those of people who've done generally ill-advised things. Though changes have been made in the past which invalidated previously spendable scriptPubKeys, e.g. OP_RETURN being made invalid closed off some perfectly reasonable scriptPubKeys.
Provided that an agreement was already reached on BIP 62, I see no problem doing the required soft fork at the same time (except for the additional coding and testing involved). Support for non-malleable transactions in clients can be added later when the network supports them.
Several of people who've been working on BIP 62 feel that its not mature enough yet for rapid deployment, as it is somewhat complicated and we've still found ourselves somewhat recently uncovering more interactions that were somewhat surprising. The strictder part of it is mature and hasn't been yielding any surprises and with that in place we can simplify BIP62 some, which will help get BIP62 deployed. It's still in progress and isn't being abandoned in the slightest.
I mean "winning" hard-fork of course. The majority does not need dead hard-forks.
You may misunderstand Bitcoin. If you are mining in violation of the network rules (e.g. on a hard fork) you are no longer mining as far as the nodes that disagree with you are concerned. 100% of the hashpower visible to a network is always in agreement with the hard fork rules.
Can't really claim to understand this fully so might be off the mark entirely.
Does this mean SSL is here to stay? I thought there where plans to move away from it and maybe even implement an alternative. Being unable to move away from SSL would be my only concern, otherwise sounds like a good move imho, +0.000001
SSL is used nowhere in the Bitcoin protocol. We do use the OpenSSL library to get access to some cryptographic functions and would eventually like to not do so, this change is a necessary step to make along that path. (e.g. if anything, the opposite of your fear).
DER should be removed it makes no sense for Bitcoin since Bitcoin has already defined the lengths and encodings of everything in its protocol.
Once you realize what DER actually is and what it does in the block its ridiculous.
Can't be
removed without totally breaking incompatibility, making people's coins unspendable, etc. It's also more or less harmless at least once most of the possible complexity is removed by enforcing strict encoding, it just adds a couple bytes of overhead. Any future CHECKSIG alternatives obviously wouldn't use it; but there are still all the already existing coins left to deal with.