Simple looks incredible. Is it as great as it looks?

It depends. I tried to switch to Simple, but at the time I was working as an independent contractor. The maximum size of a check you can deposit without mailing it to them is $3k. Having to mail in every check I received was a hassle that outweighed any benefits Simple provided over a regular bank account.

For what it's worth, last time I was doing independent contractor work, I used a billing firm, MBO Partners. They took 4% of my gross and treated me as a W2 employee. My taxes would come out of the gross, as would any benefits I elected. The rest would get direct deposited like a normal paycheck. I would have spent more than 4% of my time screwing around with paperwork, so I thought it a pretty good deal. I suspect there are other firms like this, but I liked 'em enough that I used them for 8 years or so without ever looking for alternatives.

Simple is terrific. I've been using it for about a year and 1/2. If you are already used to paying all your bills online, then this is right for you.

Exactly what I want to be doing all day: watching my bank's github repo and trying to keep up with their ever changing policies.

Edit: Mentally tracking and integrating policy reversions[0] sounds like a good time as well.

[0] https://github.com/SimpleFinance/policies/commit/b0a644035fb...