> If a piece of software I use had a bug

Probably want `used` here, right? Sticks better with the tense.

> If I had a proposed fix, you guessed it, I'd email the author. 

The interjection, "you guessed it," is usually better served by `–` rather than `,`. Maybe `If I had a proposed fix – you guessed it! – I'd email the author.`

> This workflow isn't too disimilar

`dissimilar`? (extra `s` needed)

> with a constituent services request

Is this a proper noun (name of a thing)? If not, why not `constituent service request`? Sounds like it should be `Constituent Services Request`, though.

> or lobbyist scheduling a meeting with a regulator to advocate for a particular issue as they do today

The last `as they do today` read like "Today, June 2, 2014, a lobbyist is meeting with a regulator." A comma after `issue` might mitigate the immediacy of that idiom.