That depends on how you install the 2.95 OTA updates.You would have to first flash JBear 1.58.58 right after upgrading to 2.95 to give you fastboot commands, because Jbear 1.50.50 would cause the stock rom not to boot. Then you can flash a custom recovery such as 4ext (recommended) and TWRP 2. AFter that, you can flash a rom that could run on all hboots such as Negalite Blurom. Then you can flash Jbear 1.50.50 through bootloader.
If you flash the firmware zip file it doesn't change the hboot or the ROM so you should be fine keeping what you have for those although a couple of people have gotten boot loops after updating. Those were both with CM 10.1 ROM's installed so I think it's more the ROM than the firmware.
Flashing the RUU and then taking the OTA's will automatically return both the bootloader (hboot) and ROM to stock so there should be no problem booting once that process is complete, but the hboot will need to be downgraded before flashing and booting a GB or AOSP based ROM.
ramjet73
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