I plan on buying 3 houses in 3 years, so I believe we are on similar tracks. I purchased my first home a 3/1 and have started to rent out the extra rooms. It... hasn't been an easy thing... The process will pay for itself.
When I purchased this home, I was assuming I could get maybe $600 in rent per room, so $1,200 gross rental income with a $1,350 FHA mortgage payment. I knew that inflation was coming and I wanted debt. So the 237k home price was basically free money at this interest rate, provided I can keep the property for 30 years.
I didn't care about the home itself, its location or anything like that. I cared that I could afford it myself without stretching myself financially. I cared that I got started. I did the single most difficult thing I had ever accomplished in over a decade. While feeling completely unprepared I bought a house with the intention of living with people. It has not gone well. My first roommate passed away. It took a long time to find a second, and its very likely I could be charging $800 for the smaller room and $900 for the larger one. I think those prices are crazy, but I'm not having trouble finding people for $700/$800 a month.
Now instead of kicking myself for not getting started as soon as possible I'm looking at how to prepare for a second one. I have a minimum of 10 months to save and prepare before I'm allowed to move. I can't save enough in that time frame without at least one roommate.
So lets recap...
By ignoring all the common investor numbers/math, I bought a loser and it "turned into" a winner, because the markets are crazy and I just made sure I can personally afford it. If I was paying rent like a normal person that would have accounted for a bulk of my new living expenses.
By starting I was able to participate in the rising tide effect, but I'm also financially prepared for a low tide event. You don't have to be a genius to raise your boat when the tide is rising.... just don't sink it. :)
I would focus on 2 things. 1, What risks do you think you need to prepare for? For me, it is a falling home price. It would have a negligible impact on me -- and I don't think it is likely. Falling rent prices would be the next one. Again, not something that is likely to impact me much on this first property. -- What can you do to minimize the risks?
2. How can you get started sooner, rather then later? The worst thing that can happen to you is that you stay out of the market because it doesn't meet CoC numbers. This is the first property. Don't go in hoping to get lucky, but also don't wait until you hit the winning lottery numbers either.
So long as you can weather the storms and any short term down trends getting in the market is going to be your best bet. Then, find out what you did great, and what you can improve upon for your next property. If you focus on getting started and improving as you move on you will be in a much better position no matter what happens.