Originally posted by @Jill F.:
I worked my entire professional life as a software engineer and I stuck with it even though it wasn't my passion because the job paid well and let me be part-time from home and because I was too risk averse. Now for the first time, I love my job-- I love being a landlord. The risk of being sued is always present (even as a home owner) but it can be mitigated by insurance, planning, and defensible business practices.
When you own your own business, you find out what you really value because you get to decide how you spend your time and money.
I truly enjoy building financial security for my family while providing GREAT service to a market where even average service is hard to find. The fact that we actually respect our tenants sets us apart from many others operating in the affordable housing space.
Your values rather than personality will play a bigger role in determining whether self managing properties is a good fit for you. Being a landlord isn't the right path for everyone and as others have pointed out, there are lots of ways to make money in real estate. But if self-managing buy-and-holds is the right path for you then don't let your fears stop you from realizing a dream. You might want to google risk and cognitive errors-- most people really suck at assessing risk.
Jill ... I sound a lot like you. Even though my job is not horrible, it has become stagnant and boring. I have always loved real estate. Growing up, my Mom owned her own real estate office which is how I ended up selling real estate back in the 90s.
In my current job, I am always applauded for my customer service, which I don't doubt would transfer over to the rental arena. I do always think the worst about liability. I have umbrella insurance and even short-term rental insurance with a high liability amount since I do own a seasonal rental in Arizona. The good thing out there is that renters must be over 55 so you would think they would be a little more respectful of the property. Also, payment is due in full before they get the keys (minimum one month stay). I have had my lease drawn up by a professional real estate attorney out there so I think would be covered pretty well as far as that goes as well.
I guess it just comes down to the confidence of knowing things are going to be OK if I do things the right way.