You probably won't believe this, but yes, this is a true story...
Back in my realtor days I was given a lead to a widow who lived about 45 mins away in a private community in horse country. She had put good money into restoring the property, but no longer wanted to stay without her husband, and the realtors she really wanted didn't want to get involved so they pawned it off to me (and I had no book of business at the time so of course I agreed to at least meet), and the house was going to list for well over $1 Million. Anyway, I get there and it's going well and we're touring the house and discussing what the listing may look like, and then she wants to show me the entire neighborhood. Well it's about 94 degrees that day and I'm dressed in a suit and not exactly wearing the shoes to be taking the two mile walk we're about to go on, but how am I saying no at this point? Well, we aren't just going or the walk alone -- she's going to take all eight of her dogs with us. Yes. Eight. All off leash. So there we are, walking around the private development and she's giving me backstory on every neighbor, and one of the worst things you can imagine happened -- a car backing out of a driveway runs over one of the dogs. As you might imagine, she absolutely loses it and is inconsolable and we are now over a mile away from her house (on foot) and there are seven other dogs going crazy!
The car belonged to a worker who was at that house doing some maintenance (the owners weren't home), so it's me, him, and her in one of the most awkward situations anyone could find themselves in...and finally 20 mins later she makes a phone call, and it's to someone she was letting live on her property that I didn't even know was there the whole time, and he comes down on foot as well (another 20 mins), and he also becomes inconsolable when he sees for himself what happened! This goes on for awhile, and then he finally carries the dog, and we all take a very solemn, very long walk back to her compound. We get there, I'd been up there now about three hours, and it seems only appropriate that I leave them to their grief, but yes, the story continues...
They immediately go about trying to bury the dog in a part of her yard where other animals had clearly been laid to rest previously, but they are both so despondent that neither of them are breaking into the ground. Uh huh, yes, true, yep, I proceed to take the pick axe and shovel and dug the hole. A very sizable hole, in a suit, in 94 degree heat, and everyone is a mess, including myself.
We're going to end this story there. The story does not really end there, but we are going to end it there because it's crazy enough as is. You asked, and that is my craziest real estate story. By far.
How about when your tenants use auto jumper cables to bypass the electric meter to steal electricity. The reason I found out about it when I did is because I seen the tenants on the local news at 10. Arrested for selling meth, having police survelence equipment, and Posession of a pipe bomb.
They wore their jail orange jumpsuits to the eviction hearing. Hmmmmmm.
@David MacClintock I walked through a house (for potential wholesale) that had horses living in the basement once. That was bad
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