Its not the amount of solder Jim it sounds more like the technique not making them stick. Try this...
Tin your pads by setting the solder on the pad then setting the iron on top to melt the solder. Tin your wires as normal. Now clean and tin your solder iron tip, set the wire on the pad and then touch the soldering iron to the wire. When it settles into the solder on the pad remove the iron and DO NOT blow on the joint to cool it. That's a newbie mistake that instantly makes a cold solder joint. If the smoke from the flux is an issue then blow high over the board to keep clean air in front of your face and not down towards the board to cool the joint.
If you do this a few times to get the hang of it and reputability you will never have another bad joint again.
You are correct. Certainly the big factor in the solder connection is the quality of the joint and not the quantity of the solder, so yes I always tin both items to be connected.
My issue is the tiny space/close proximity to work in. Because it's so small I have to be extra careful about the amount if solder. Additionally because of its size and delicate components I also have to be careful of overheating adjacent components. So while I do solder this as you suggest, I don't like pushing soldered joints together like this with the iron as it's a balancing act trying to not use too much heat and roast a component nor too little and get a cold solder joint, nor using too much solder and bridging a point or too little and not providing a good bond.
I think next time around I might try alternating pads on the board to give myself more room to work. I also ordered a new iron (temp controllable) and an extra fine tip.