You got some good opinions and pointers. In my case, I bought older properties on the cheap in high appreciating areas, knowing the properties need some work. That's in NYYC. I was not a big landlord, but owned a number of 3-plexes, and had up to 20 units total at one point, and the problem with leaks from upstairs occur one or twice and year, spent on the average $1,500 to fix, but I never requested the tenant's reimbursement.
Let me tell you why.
I've been doing rentals for nearly 40 years, and my dad before that. My dad had a mixed use property among some large apartment buildings, some with over 100 units. We often hear of controversies between landlord and tenant for this.
Where there's a leak in the ceiling, some are discovered right away, some are discovered months later. In the case of "strict" landlords, when discovered, people would deny knowing about it, even though they do. In these cases, plumbers have to check for leaks in pipes in the walls, under the bathtub, sometimes cutting holes in the ceiling. In the case of tub and toilet overflows, the plumbers find nothing, you can't prove the tenant is at fault, but you leave behind a pissed off tenant, if in fact they are really not at fault.
Think of all the money you saved not cutting open walls and patching them up again where in fact it was an overflow, and the tenant old you that up front.
I'm more easy going, so if something happens, people tell me right away, and that in itself prevents more damage. I have a SFR that makes people responsible for repairs under $100.00. Before that, when there's leak under the sink, they call me. With the $100 responsibility, they don't call, put a pail under the sink, and damage occurs when they forget to empty it.
Unfortunately, my mother in law who owns rentals, are of the old school, gets after tenants for everything. What do the tenant's do? They get after her for everything. One got after her for lack of security for a break in, after a few run ins with her, and demanded over $5,000 in damages. The city got involved with code violations. I finally helped her with the tenant giving him a month and a half free rent, around $1,500. The insurance agent suggested not filing claims as the insurance company can cancel the policy and raise rates. The tenant was with her at that point for about two years, and she did charge him back for a number of minor things. I finally told her, you got the money on a bunch of small things, so where did that get you?
Oh, you got some wonderful information on the overflow pipe in the bathtub. Of the average of one or two complaints a year on leaks from upstairs, the plumber found the problem with the overflow pipe in one case. Currently, we found damage caused by overflow with one tenant, and it was caused by overflowing toilets. As I said, I'm easy going. If it was my mother in law handling it, they would deny they know anything about it.
Most of the leaks from upstairs in my rentals come from pipes in the walls, for buildings over 50 years old, pretty common, people who didn't know how to use shower curtains, defective shower doors etc. The funniest one was the wax seal under the toilet was leaking, and the plumber called to ask if my tenant is a heavy guy. I said "yes. he's about 275 lbs". So he said, "I seen it happen, an old toilet, a heavy guy who sits and squirms on the toilet would do it". What should I do, charge him for the repair since he squirms on the toilet? What if he says "I don't recall ever squirming on the toilet"?
One word about renter's insurance, they don't allow it in NYC although I asked tenants to buy it. I had one wise guy who bought it, sent me proof, then cancelled it a week later. Some month's later, he left his windows open and caused over $6,000 in damage, floor boards all buckled. Tenant even wanted to get after me for damages to his property. I said, "you got $150 back on your renter insurance and now you're out $5,000. How did that work out." I filed a claim in this case, the one and only in nearly 40 years. They didn't cancel me or raise my rates.