Made An Extra $100 and Why I Am A Terrible Landlord

My current rental house guest called me yesterday and wanted to know if he could stay an extra night because he needed more time to pack up. Sure, I said, no problem. Just give me an extra $100. Actually I said, "Would $100 be OK?", knowing full well that I would take less if he resisted. He said, "No problem". Whew. I am terrible when it comes to being assertive. If I had charged the full price for an extra night it should have been $130. He showed up 2 days early too and I only charged him $100 for that. I know some people love having rental property but I am not cut out for landlording. I don't want to hand it over to a management company either because their fees are outrageous, it has to be unfurnished (which means I wouldn't be able to move back in while it was vacant), and there are too many unfurnished houses for rent right now. As soon as I can sell this house it will be a huge weight off of my shoulders. I have enough money tied up in my other vacant land anyway so I think I am still well diversified if I sell the house.

Tomorrow I will go over to the house to get my $100, wave good bye to my guest, and scrub the house until it sparkles again. I have another possible short-term renter who wants to see the house before he commits to renting for the month of March. The good thing about being a furnished short-term rental is that I get all of the rent up front and my guests are just visiting so it is very unlikely that they would refuse to leave leading to the expense and hassle of an eviction. Also, since most are from out of town, they have to trust me more than I have to trust them. They send me the check in advance and I cash it before they arrive so I know their money is good. They have to trust me that my house really exists since they have only seen pictures and the house still doesn't show up on map searches like mapquest.com. Mapquest shows the location of my house to be on a dirt lot across the street and the aerial photo is 3 years old so most of the houses on the street are still under construction. I am amazed I get any guests at all!

One of my coworkers has 3 small apartments that he rents out in a small town. He gets plenty of renters but the quality is very low. He doesn't require any information like employer, credit check, or references. One of his last tenants was in jail and then deported. Another left without paying the rent. He just rented one apartment to a pregnant single woman with no job. I told him he should register as a non-profit organization because he is running a charity. Maybe at least he would get a tax break!