Hello
without looking at you config its hard to understand - however looking at the design
1) advertising the same subnet out of each ISP router would be applicable for resiliency
2) asymmetric routing could be due to the isp2 return scr traffic seeing the your rtr2 as a shorter path back into your network -( maybe bgp path manipulation could help here-as-path pre-pending?)
NOTE:
faiilover of either router ISP link would cause traffic to be routed back over you LAN via igp -a more positive approach would to put a interconnect link between each router and run IBGP this could also help with path manipulation for outgoing traffic ( local preference)
3)Not sure on this one -if you can connect to this server then I am assuming the iOS fw has allowed access -possible folder permissions etc....
res
Paul
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Kind Regards
Paul