Altium Designer - connection of two nets and using vias
You should definitely use a polygon pour or an internal plane that you can drop the vias down to and connect them together. This is very common practice and has numerous benefits besides just connectivity.

As for the serpentine traces, Altium includes a tool to do this for you called "Interactive Length Tuning". It's used to add length to certain tracks in order to make them match the length of other tracks where timing is critical (i.e. high speed data signals and clocks). You can learn about the tool here:

https://www.altium.com/documentation/18.0/display/ADES/((Length+Tuning))_AD