However I'm wondering what other expenses have come up, perhaps on a yearly basis (or even less frequently) that I should be considering in my calculations?

We're thinking we'll be able to get started within the next year so really concentrating on building my knowledge base of the industry as well as the surrounding markets now.

I do frequent the Black Diamonds meetings, there's a meeting coming up next Tuesday June 20th let me know if you can make it and maybe we can have a drink.

As an appraiser, I frequently find myself in a tough situation - I believe the value of a property is there (contract price) but the comps and market data show that it isn't.

One of the nice features is that you can define locations like addresses where you have properties, the usual stores or services centers that you frequent, etc.

If you move out in a few years to house hack another property, you'll still have those benefits and they'll definitely help the first property toward cash flowing better.The question of "bigger down payment on fewer properties, or lower down payment on more properties" comes up frequently on Bigger Pockets so I'd recommend searching for similar posts and seeing what comes up.In general, for newer investors my recommendation is that because "you don't know what you don't know" (i.e., this is mostly all new), that you put a larger down payment on one/fewer properties to give yourself a safe buffer for learning, for the market to turn against you, for expenses you didn't anticipate, etc.

These turn-over a little more frequently and their time on market varies.Residential properties with 2-4 units come-up fairly frequently, but, in the past 3(ish) years tend to be over priced.If you would like to compare notes or have questions on any particular property, feel free to PM ... if it has been on the market for an extended period, there is a good change we've looked, maybe even analysed it, and might be able to provide some information.

Austen, talk to @Steven Hamilton II, he works with real estate investors, based in Illinois and also frequent contributor here on the forum. 

There are clever ways around it frequently discussed on these forums. 

IF I were you I would concentrate on the debt first to eliminate potential financial problems in the event you hit the inevitable rough patch should you decide to move forward on the rental.