Ouch, this one hurts. I lost my Dad to pancreatic cancer last year and had a very similar experience - he loved jumping on the tractor and cutting the grass on his little farm, but we went so quickly from him asking me do it temporarily while he recovered from surgery to him never getting on the tractor again.
So sorry for what you're going through, and wishing you some peace wherever you can find it. My email is in my bio, please reach out if you need someone to talk to (I have no useful expertise or advice of any kind here, but will gladly lend a listening ear).
When I moved to my current job a year ago, I shut down my business and closed a checking, savings, business checking, and credit card account with Bank of America. I had a Simple invite sitting around, and thought it made sense to consolidate and...Simplify, making my single Simple account my sole bank.
I couldn't be happier with that decision, and believe that I have been saving money (in both fees and in general) because of Simple's interface.
So with this news, I feel excited for their team, but still very nervous. I joined Simple precisely because I was tired of dealing with a megabank (like many folks here), so if Simple can continue to buck the trend and stay customer-focused and agile, then I'll continue to be all-in.
I've downloaded the client, added an app (Django, Rails, and Node). When I tried to view the page, it 404'd and then promptly walked me through SSHing in and starting the server process.
I'm impressed.
Later in the day I'll dive a little deeper, but between frictionless "add an app" process to the way it feels like a local development environment - I think you've got a winner here.
After asking lots of questions, I was pointed to http://make.wordpress.org/core/handbook/, which does a pretty decent job outlining the workflow. It helps to read a lot of tickets first to get a feel for what they're fixing - http://core.trac.wordpress.org/report/14 and then find a neglected (but fairly recent) but and chip away at it.
It's overwhelming, but I've found a great amount of confidence in just picking a (tiny) bug, fixing it, and watching the process work. Good luck to you!
I'm a Googler and would be glad to show you around one afternoon. Shoot me an e-mail (address is in my profile) and tell me a little more about yourself and we can work out the details.
(Edit: También hablo Español si te hace sentir más cómodo.)
Kirby came to my attention about 6 months ago, and I'm just getting around to playing with it. I'm highly impressed with how easily it can be extended and customized.
By the time I'm done, I will have an extremely lightweight static-file based blog that syncs with Dropbox (and has a web-based control panel, if needed). The tutorials on the site are great to get you set-up. Highly recommended.