Now I'm collecting $1300 a month rent from the other tenant, which covers almost all of the mortgage and taxes. Upkeep isn't that big a deal, since the way my lease was written, I was already responsible for all of the groundskeeping and snow removal when I was renting anyway. Also, it's worth it to make sure you have good tenants, that pay on time, and don't make a mess.
After the initial fixes and repairs we had to do during the purchase process (every home in California has termites), I've been working to automate as much as possible. Here's my "Landlord Stack":
1. Cozy for applications and rental payments (https://cozy.co/) (Price: free)
2. Rocket Lawyer for leases, other documents, and random law questions (https://www.rocketlawyer.com/) (Price: $50/mo)
3. Xero for accounting (https://www.xero.com/) (Price: $9/mo)
4. Trello for organizing information and to-dos (https://trello.com/) (Price: free)
5. We bank at Chase and use their online bill-pay to handle the few utilities we're responsible for.
So for I've had to unclog a couple toilets and fix a window screen. Other than that, smooth sailing so far. Email in profile if you want to get in touch.
The single best piece of advice I can give is to provide a great experience for your guests and have a high price to match that experience. No factor I've found better judges the quality of a tenant than the ability to hand over a big wad of cash.
But I've seen enough stories about nightmare situations that I'd rather cover all my bases before jumping in.
He comes across as a great guy (heard him interviewed on a podcast before I bought the book), has a really readable style (seriously, it makes real estate financials "light reading"), and generally seems focused on helping people (he was apparently teaching when a publisher approached him to write a book - he told them he wouldn't write the book they wanted because he thought it would be useless, but he would write them a book on what he thought would be most useful).
And absolutely: if you're from a comp-sci background, the real estate math is all trivial plug and chug. But it is worth learning the accepted ways of doing things so you can properly compare and model your properties.