Ack, ack, ack ...
(sorry ... hairball)
Actually ... tinning can help, but I find it also weakens the connectivity, especially if your gear has spring clips. I strip the wire bare, then give it a quick one-two with some 00 wool, then flatten it with a pair of flatnose pliers prior to inserting it in the clip. Maximizes the contact it does.
Same holds true for terminal and post connectors, but not as bad because you can apply more pressure to increase the contact.
Rather than tinning, I'd suggest a touch of DeOxit Gold every now and then. Leaves the wire flexible to fit the connector and also increases the quality of the connection. Stuff's expensive, but that little bottle goes a long way.
Goes without saying it's a good idea to leave yourself some extra when cutting new wires for refreshing the ends over time.