1) does bridges like obfs4 work properly within latest whonix?
Yes. For obfs4, wait for Whonix 11. [Release announcement most likely later today.]
2) is it just like configuring normally within the tbb?
No, unfortunately not.
Bridges in Whonix have to be configured on Whonix-Gateway. Manually. Using /etc/tor/torrc. Not using TBB.
- you don’t have tor-launcher (= Tor Browser Essentials) available
- you cannot use the pluggable transports that come with TBB
See Configure (Private) (Obfuscated) Tor Bridges.
is it true bridges are more vulnerable to attacks and user profiling than normal entry guards?
A general Tor question. Please see this discussion (linked from Whonix https://www.whonix.org/wiki/Bridges documentation) but copied here for your convenience: