That’s a neat looking trick, will have to see how well it works in practice. I can’t see it working too well if you need to feed the wire into a through hole.
My trick is to tin the joint and the wire, apply no-clean flux to either the joint or the wire (situation dependent), then bring the two together while reflowing the joint. Quite handy for soldering tight multi-pin connectors.
The real tip is buy flux, it’s just as important as solder.
Agreed on the through-holes, and doubly agreed on the flux. All magic in soldering ultimately comes from flux.
The other way you can easily solder to pads is to use solder paste. Many people don't seem to realize that paste is good for more than just reflow. It's not as useful for situations like this, where you need a relatively large solder volume (so I'd also use your method), but it works quite well for smaller scale work.
My trick is to tin the joint and the wire, apply no-clean flux to either the joint or the wire (situation dependent), then bring the two together while reflowing the joint. Quite handy for soldering tight multi-pin connectors.
The real tip is buy flux, it’s just as important as solder.