After my bad experiences with renting an apartment in Chiang Mai, I was definitely turned off on renting anything here for a long time. Returning from Tachileik, Myanmar for my visa run, I checked in to Buddy Guesthouse on the east side of Chiang Mai's old city, near Tha Pae gate (which means bamboo boat gate, since it used to be a dam, I think).
My plans changed as I ended up staying at Buddy for months. It was much more comfortable than in the apartment. And even though it was called a guesthouse, it was more like a nice hotel.
Since the WiFi was great here, I started spending nights working in Buddy's downstairs lobby which was like a nice open terrace, and I would be chatting with the Thai staff. The staff consisted of 26-year old Jin and 25-year old Johnny. They would keep me company during their night shifts at Buddy's front-desk. It was awesome as Jin & Johnny quickly became my best friends in Chiang Mai and I ended up hanging out with them a lot as well as partying a few times.
There was a potential problem though, hotels are significantly more expensive than apartments. But I knew that if I could speak to the manager I could convince him/her to make me a good deal. Thais love deals. Since the hotel management knew I was friends with the staff now and was a clean guest, I managed to get a 50% discount on the day rate for the room by staying for a month, which significantly reduced my monthly spendings. I was now spending 6x less on rent than when I lived in Amsterdam. And the rate even included daily clean towels, daily room cleaning and WiFi for free. And this felt much better than my 110m2 (1200 sq. ft) Amsterdam apartment, that was too big any way.
Living in a Hotel