Yes, your workflow matches what I'm suggesting.
Palo Alto GlobalProtect already kinda does this, as does MS DirectAccess. You connect to a "portal" and that portal can have multiple gateways. In our situation we have data centers in Minnesota and New York, which multiple endpoints/gateways in each data center on diverse carriers. If one has issues or is performing poorly for a given user or set of users, we currently suggest they switch to another endpoint/gateway.
They are already accustomed to losing their VPN connection during the transition of disconnect -> reconnect.
You could do this within folders, or we could use <connection> bloxks within a single configuration with some agreed upon comment like:
<connection>
#tb: New York 1
remote x.x.x.x 1194 udp
</connection>
<connection>
#tb: Minnesota 1
remote y.y.y.y 1194 udp
</connection>
...
And so on.
There is a related feature, if this were implemented, that could be useful. In the case of PA GlobalProtect, they provide a "best server" option where, when selected, the client performs a quick analysis using ping and traceroute to figure out which server/gateway is closest or fastest, and connects to that one.