For encryption, the client and server need to share their private keys.

This is incorrect, for asymmetric (public-private) encryption. You never, ever share the private key, hence the name.

The private key is only used on your system for local decryption (someone sent a message encrypted with your public key) or for digital signature (you sign a document with your private key, which can be validated by anyone with your public key).

For the server, they are signing their handshake request with a certificate issued by a known certificate authority (aka, CA, a trusted third party). This prevents a man-in-the-middle attack, as long as you trust the CA.

The current gap is in inconsistent implementation of Organization Validation/Extended Validation (OV/EV), where an issuer will first validate that domains are legitimate for a registered business. This is to help prevent phishing domains, who will be operating with TLS, but on a near-name match domain (www.app1e.com or www.apple.zip instead of www.apple.com). Even this isn’t perfect, as business names are typically only unique within the country/province/state that issues the business license, or needed to be enforced by trademark, so at the end of the day, you still need to put some trust in the CA.

The games in progress I mark as favorites, I have “Finished” and “Play Next” categories, and I have a big dump category called “Won’t Play”.

Aside from that, I have some big categories for collections of old games from humble bundles and steam sales, like legacy Myst, Wizardry, or Sierra games, or like Star Wars game collections.

How diverse is your investment portfolio? How many different stocks and securities have you sold last year? Were these subject to short term or long term capital gains? Did you rebuy any of those, making the security subject to the wash rule?

If you have a family, a house, multiple W-2s, 1099s, a retirement account, and a 529, things are still pretty “simple”. TurboTax does not let you use their free file if you’ve traded stocks, but for most other products, even some low volume trading in a brokerage account is considered fairly standard.

At the end of the day, it comes down to how organized you are, and how much time it will take you to do data entry. Usually, your tax documents have clear headers, and usually, these match up to the fields in the tax application. But not always, and the more documents you have, the more hours it will take, and the more likely you are to run into a speed bump that will cause frustration.

So, how much is your time worth to you? If it’s worth more to you than the cost of a tax professional, it’s an easy decision.