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I know you asked for interesting stories but it seems respondents took a different tack and decided to offer advice to perhaps prevent you from having your own "interesting" stories. I will join that line....
Finances, don't ignore finances. More people that have failed because of finances than other reasons.
It starts with buying the right property for the right price. What makes a good rental? What is its turnover going to be? What will the depreciation rate be? Do you want a lower or higher depreciation? What is the appreciation potential? Where do you expect to make your short and long term profits?
Do you want A tenants, D tenants or something in-between? It is key to set the proper rent price to maximize your profit and keep your tenants. Normal business calculus here
You need to estimate your operating and reserve expenses properly. There is a high failure rate if a large repair comes up and you are underfunded.
And, finally, taxes taxes taxes. What good is all of this if you overpay your taxes. There are significant tax advantages of rental property(ies). But you have to be aware of them and take advantage of them. I highly recommend learning this subject yourself as it pertains to rentals. This subject is not well understood even by some CPAs. Most do, but how do you know? Trust yourself. And you should have a good idea before buying your first property because some decisions may be impacted.
Oh, one more thing - I would have only studio apartments, and maybe a couple 1 bedroom apartments. I'd give current tenants first dibs on the one-bedroom apartments and have a waiting list for them.
This prevents large, noisy households. But, if a current tenant wants a bigger apartment because they got married or are going to have a kid, then you can keep that good tenant. I had a couple that did this until they could save up to buy their own place. Worked out great.
But, honestly, all studios would be even better. You probably only have to allow 2 people per studio. Works out to a quieter building overall.