Earlier quoted context omitted.
Wow, I wish. I'm speaking as someone who put all his retirement savings into index funds year after year, but then married someone whose job is related to real estate. Real estate feels more concrete and understandable to her than finance, so that's where our money goes now. It's not easy free money, and I don't know why you would think that any high-profile, low-barrier-to-entry investment would be easy free money.…
Are you spending an unreasonable amount of time managing property vs the rent you take in? I spend a max of an hour a month on average on property management. Find good tenants (reduce the rent if you have to). On average my tenants have had 3+ year leases with minimal management.
Finding tenants has taken a significant amount of work as well. There are commercial brokers that act as matchmakers, but you still have to meet with the tenants, walk them through the space, talk about what kinds of modifications they want, figure out if the timelines are compatible, and do a little bit of due diligence. She does quite a few of these where the details don't quite work out because the tenant is looking for a different style of building, easier in-out for the parking, improvements we'd never agree to, etc.
The process of transitioning the properties to commercial was also time-consuming. Commercial has entirely different requirements, and upgrading the parking, accessibility, etc. took a lot of time, money, and back-and-forth with the city.