I had a lot of trouble ever getting the ESP-01 to work with a CHI based serial to usb connector. Once I used the FT232 based adapter like this:
http://www.ebay.com/itm/201332938880?_t ... EBIDX%3AIT
It worked perfectly. With the DTR and RTS you don't have to manually push any buttons or manually pull up or down any pins in order to program the the Arduino IDE. It just works!
Wire it up like the first diagram on this page
https://github.com/esp8266/Arduino
Minimal hardware Setup for Bootloading and usage section of that page.
It should work great.
Now this can have issues with the serial monitor. Perhaps the 1.6.5 IDE has fixed this... Have not tried it yet.