For the ongoing/routine items, I'm less sure - though have a pretty good idea of some routine stuff, like lawn mowing, other things feel like a complete guess, like how many plumbing calls will I'll need per year per unit? 

Luckily I was able to convert a portion of the front lawn into an additional parking for not a lot of money, but I had initially failed to account for this inconvenience - lesson learned.  

Option 1 is clean and easy and everyone walks away, and they don't have to maintain the utilities or the lawn while you are trying to find a new tenant plus keep paying rent. 

So, as a technology entrepreneur, I got to wondering if there's a way to research, acquire, and manage my deals more easily using the power of artificial intelligence (AI) or some other internet software.I have an idea of what I think I need to build, but before I build it, I would appreciate some feedback from this community: What's the hardest (or most frustrating) part of real estate investing for you?

Don't we think investing in the US is risky with high interest rates, historically low affordability and cash flows and high prices inflated by 15 years of artificially free money that's gone for good?

Of course we still maintain insurance on it and have a lawn guy that takes care of upkeep.

Sometimes properties with clouded title are sold using owner finance.5) Talk to a property manager to ensure these are good rental areas and the rental income is not artificially inflated by an unethical seller.6) Do the math on the repairs, monthly income, monthly expenses all make sense.

She then tells me " I cant cut grass , I am a woman and I dont even own a lawn mower "    I told her that the lawn mower doesnt care what gender you are , and if you dont want to mow the lawn I can arrange to have it done for an additional $ 100 per month added to the rent .    

I am told from the person who mows the lawn that he does not have a phone, and she only hears from him once a year or so, when he mails her a check for her services. 

The neighborhood is nice, quiet, lawns taken care of, no junk cars sitting in driveways or the street, with a small HOA payment monthly.