My first rental investment property was a 1980 built triplex in south seattle, bought 2006. three 2br/1ba units. This was near the top of the last RE bubble for seattle, so I probably paid too much but I had to make a full price offer (at least no escalation clause was needed) to beat out other buyers. I had looked at a lot of similar 2-4 unit properties over the prior several months, and this one despite being in a challenged neighborhood (for the time) was the best option and had some amenities I wanted for a place I was going to live at for a few years.
I used 30 year conventional FHA mortgage, and rolled all the proceeds from the sale of my SFR into it, so I came in with about 50% down on a $410k purchase price. That got refinanced a couple times in the intervening years.
I lived in one unit, used the basement as my workshop, and inherited 2 good tenants (lucky) from the prior owner. At the time the rents were $765 and $800.
This was my first rental property and my first experience as a landlord. I was and am good at fixing/repairs (I come from a DIY family and spent prior 6 years fixing up my SFR, pretty much all aspects) but I didn't know too much on the management/investing side, so I took a few local night classes to familiarize myself with that.
I self managed this property (and subsequently purchased ones) up until March 2017 when I hired a PM, mainly in response to Seattle regulations, to position myself for further scale, and to get some free time back. (I have a day job too)
Since I was owner occupying one unit I wasn't too concerned about cash flow, but the rents vs. purchase price would have worked out to about 5% cap rate on actuals, that was about the going return for south seattle small MF's at the time. (north seattle, like now, was well below that)
I still own the triplex, Today market rents are about 75% higher than they were when I bought, and I have fully renovated the building and added value via various improvements. Its almost paid off now, I'm debating various options. Its solidly in cash cow territory right now and zero deferred maintenance, but my ultimate plans are trading up to something bigger.
As for what I would do differently:
I got fairly lucky on a couple aspects with the triplex buy, beating other bidders and getting decent tenants from the get go. I did pay my dues in dealing with a lot of deferred maintenance and dealing with a rough neighborhood for the first few years especially. A little nicer area would have reduced that drama and attracted more quality potential tenants during vacancies. I was (and still am) probably more conservative about leverage than many people on this forum. I am doing just fine but I could have grown faster with somewhat more leverage and being more aggressive about collecting more properties sooner.
I'm not great with networking/door knocking to find off market deals, I probably could have found some stuff doing that, especially 2008-2011 time frame (when I bought my (listed) duplex - not a bad buy but there were other properties that came and went for a similar price that would have been larger/better if I were more aggressive and had jumped sooner)
Like many first time landlords, I was probably too chummy with the tenants and probably should have been more aggressive with rent increases over time. I did make 2-3% increases most years while I was self managing, with the PM rents have gone up 15-20% in the last year and a half, and I'm still about 10% below market on most units (I have a lot of LT tenants). However, the stability and risk reduction as a newbie wasn't all bad.