Current Pain Points

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This page is for an up to date list of professional, technical, knowledge etc type issues I'm currently grappling with.
Note: the point isn't to complain. Instead it's part reflection, part invitation (definitely interested in any thoughts or resources,
Also, as someone always on the lookout for new software ideas, I think it's interesting (and often valuable) to hear people talk about pain points. Maybe others find it interesting too.

Update 2020-09-28.

Putting these in writing (in public) for a few days has already made them seem more solvable, in a good way. My higher agency self is already saying:
These are your pain points? These are enough of a problem for you that you created a separate page to list them on your site? Creating a good plan to solve these (with contigencies etc) might take a day, at most.

1. Classic Books that Are Out of Date

I'm a big fan of learning via
in general, and there are a lot of books I really like that a bit out of date.
For example, I really like Gabriel Weinberg's
and Rob Walling's
Start Small, Stay Small
but both were written in 2010 and definitely are dated in parts.
Traction is a comprehensive list of traction channels and seems very good. But it doesn't include things like going on podcasts. With the big emphasis in the book of "the law of shitty click throughs" and channels getting stale, it'd be nice too have a comprehensive list that's a bit more up to date.
Start Small, Stay Small
is great too, but some of the, e.g. ways to evaluate niches, involve tools that aren't even around anymore and/or methods like looking at magazine subscription numbers that probably are no longer ideal.

Preliminary thoughts on solution

Probably just sitting down and thinking. To the extent marketing and niches are competitive, it might even be an advantage that information like this isn't as widely available. More up to date information might be found in non-book channels too, e.g. MicroConf talks.
But if anyone has any recommendations or wants to take a crack and writing these let me know.

2. Dealing with Moderators on Reddit

The bulk of my initial traction for my book came from Reddit, via a few posts like this:
Each of which got 1k+ upvotes and multiple gold/platinum awards (still not sure what that means). After two posts like that (an initial one and an update a few months later) I had over 3k people on an email list.
It seemed like a win-win, it was obviously something people were interested in (over 97% upvoted) and it gave a promising traction channel, which I needed if it was going to be worth it for me to do.
After the book was out and doing well, I decided to look at a baseball version. I did an initial post on r/baseball, which for a few hours was on a similar trajectory to my initial r/fantasyfootball post. Then the mods took it down, despite the upvote rate (95%), positive comments etc.
I understand reddit moderators have to put up with a lot of crap, and user experience would suffer if 80% of posts were people trying to sell things. But it was definitely frustrating to have a positive, highly upvoted, seemingly win-win post removed, especially as a critical traction channel.

Preliminary thoughts on solutions

I've actually thought about testing out reddit ads. I (and most people I'd guess) usually ignore them, but I've usually had good responses to my posts, so it's probably worth trying.
If not I guess I'd either have to ingratiate myself with moderators (not nec always possible) or find another traction channel. I suppose traction isn't always (or usually) fair, and if making a promising traction channel work means sucking up to reddit moderators or making more of an effort to comment in order to become more visible, so be it.