First time SFH buying experience in Chicago

[Daniel Shafer]

Hey everyone! I've posted a couple times here and lurked a lot more over the years and now that I've made the jump from potential real estate investor to actual real estate investor, I wanted to contribute some stories and observations back to the community. Hope you'll find it helpful or at least interesting. I think the main people who might benefit from this post are other new or prospective investors since the experienced among you would probably find all this pretty basic. I'll be hand-wavy with names/places/numbers because I don't want to overshare but am happy to call myself out for missteps along the way.

For the first foray into real estate I purposely didn't want to overextend myself because I'm very much still in the learning phase. So I got one that was very in-budget, good in terms of cash flow, decent neighborhood, not too old, clean inspection, etc. The biggest lesson I learned is that things take a lot longer than expected and cost a lot more than expected as well. Maybe I should have done more research and maybe things usually do take this long or cost this much, and so on, but overall I was very surprised. My offer was accepted in July and the transaction didn't close until September, and because the property manager holds on to rent for most of the month, I didn't get my first month's rent payment until this morning. I was bidding on and off for properties for a couple months prior to July as well. So let's say it was 4-6 months from when I had the full intent to buy to actually seeing money come in and not just go out. 

In terms of the purchase process, just about everything that could get delayed did get delayed. Things like an inspection not happening because the tenant wasn't home, or a transaction coordinator forgetting to respond to emails for a week or indefinitely because of eventually changing jobs mid way through my purchase, were pretty par for the course as well. It's a good thing I have other things going on in life besides real estate because if this was my main thing, I would have been sitting around most of the time, for a long time.

Let's talk about costs. As a percentage of the downpayment or of the house value, it was really really high. I don't have the exact number/percent off the top of my head but want to say it was in the neighborhood of 10 thousand dollars for a pretty modestly sized/priced SFH. The last sentence of the previous paragraph also applies to finances because you'd be surprised, and certainly I was, at how many people come out of the woodwork to charge you x hundreds of dollars for this, x thousands of dollars for that, and so on. 

Admittedly I've had a somewhat downer tone up to this point and so will switch to some positives and learnings. The first one is that the house occupied by a tenant who's current on the rent and so I never really had to worry about whether the mortgage would be covered. The second is that the folks you partner with can be a pain to deal with or a helpful asset. I was fortunate in that there were more of the latter than the former in this transaction. Then again, I was and am paying them a decent amount to be attentive. 

This is starting to get long so I'll wrap up the musings soon. Overall, I'm happy to have gone through this process and it's cool to know in the back of my mind that I own a house now. I'm not super in a hurry to do it again because of how high the transaction costs were and the other investment competing for my dollars is that total stock market index fund which has $0 transaction costs, .04% management fees, a decades-long track record, and all I have to do after buying is...nothing at all. In terms of other options for where to go from here, there are things like participating in syndications, but I find the fees for those unacceptably high and favoring the syndicators at the massive expense of their investors. I could also move on to multi family so that more units are acquired per transaction but wonder how much of a different beast it is than SFH and if I'd have to start competing with institutions and folks who invest full time, are better resourced, and have creative financing options that I'm unaware of and/or are inaccessible to me.

Thanks for making it all the way to the end! I welcome your any of your thoughts and ideas