At first: Thanks a lot for testing and your impressions!
Important note for BETA versions:
There is the SD-Card-Image Beta (Jessie Image) AND the Max2Play Update Beta (> 2.28 for testing). The Max2Play Beta Update can only be run with a activated licence and can be found on the settings page in the web interface. For the Bluetooth Addon there are some changes in the main Max2Play version that are not coming with installation of the bluetooth addon.
2 different versions of the Bluetooth Addon:
The Jessie Image and the Old Wheezy based Image of Max2Play do have a complete different Bluetooth Support. Using the latest Max2Play Update both should automatically connect once the BT-device that is choosen on the Bluetooth addon page is powered on. Only the last choosen BT-device will be automatically connected. Right now it is not possible to connect to more than one BT-device at a time. When you want to switch to an other BT-speaker you have to choose it in the BT-Addon (click reconnect).
You need the Beta-Updates of Max2Play to get the autoconnect functionality for squeezelite without the need of restarting
I never tested with the RPi V1 but it should work. Your Squeezelite player seems to have trouble to connect to the Alsa bluetooth-device. Your settings are fine and the BT-device is connected (very good). Maybe some other audio player is blocking the audio-device. Try to stop Shairport and Kodi (if running) and restart Squeezelite. If this doesn’t help, you may give the Jessie Image (Beta) from our Download-page a try as this uses another way to play the audio.