Regarding first issue:
Have a look here for a correct solution:
http://wiki.squid-cache.org/ConfigExamples/Intercept/AtSource


#Example for squid and NAT on same machine:
iptables -t nat -A OUTPUT -p tcp --dport 80 -j DNAT --to-destination
SQUIDIP:3128
#Replace SQUIDIP with the public IP which squid may use for its listening
port and outbound connections. 

You are redirecting port 8080 ... That means, you have a proxy explicitly
set up in the brwoser. 
DO not do this for transparent squid. That's the purpose of the steup :-)






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