It would depend on what you're drawing. I think I can safely say most things are more convenient to draw without negative space considerations first.
I would note, though, that for design work, it could be useful to start off a painting with negative space, but only in some cases. Specifically, cases where the outline of something really matters. This could also apply to cases where the use of space is very important or you are not sure of a silhouette of something yet. It comes to mind that abstract and other types of work heavy on design elements/constantly changing shapes could be suitable for this method.
For the first case, I mentioned cases where the outlines of things really matter. If, for example, you are designing some hairy bugs lol (it's more common than you think) and you are not sure of what the bug you are going to paint will look like yet, you can put a dab of negative space paint (depending on whatever color the background of your main focus bug is) on your canvas and push it around until you start to see something in the positive space aka the unpainted space on the canvas. I know no one who uses this method, as it wastes paint, but supposedly, you could do that if you were still stupidly indecisive about what shape your hairy bug or whatever you are painting will be. Normally people do the design stuff with pencil and pen on paper, but I guess the richer ones can do it strait on canvas, mess and all. lol This is very suitable to do digitally though. Digital paint is free of charge, no mess included. xD In photoshop and other programs, you can just put some black on a blank canvas and push it around until you find a shape you like. Then you can go in and do positive space work. I do have to say though, most people think regarding positive space first, not negative space. No one thinks about the shape of the air around the donut. They think about the donut first. lol
This could also apply to cases where use of space is very important. Like where you have a picture of something and you need to draw it correctly up to the last detail or something ridiculous like that. Maybe photorealists do this. I don't know. I do know that a lot of artists draw backgrounds (aka negative space) before drawing foregrounds though. It's standard practice for some artists for some reason. I forget why, but pencils are always placed on canvas before starting to put on paint for negative space, so I don't think that really applies for the condition of "negative space first"....though maybe second! xD lol This could also be useful for doing "grid drawing", where you draw identical grids/similar grids on two surfaces, so that you can look at the little boxes in the grids and better judge where things will go. It's a pretty looked down upon thing though, not common by any means. Drawing grids is seen as a shortcut so that artists don't have to judge things by basis of measuring fractions and angles, but instead using the boxes as reference points. Drawing grids also takes a while and is a hassle to do, really, so I don't know. I suppose you could do negative space first with the grid method as to avoid making further mistakes, but if you're so desperate as to using the grid method on canvas (poor soul lol) it might actually help.
And then the last one, if you're not sure of a silhouette yet. Well, this is mostly for the abstract people. Generally, all other styles of art depend on you doing some type of planning before going gung ho on the canvas and splashing paint around. For abstract art, you can just dive straight in. I'm not even sure abstract art has any sort of conceivable negative space, but I guess the secondary/tertiary elements of a piece, that are behind a main focus can be painted in first, paint pushed around until a suitable negative space is filled, and then taking some other paint for elements nearer to the primary focus and painting on top. So this is one case where it's definitely possible that it can be convenient to start off a painting with negative space.
But yeah, generally it's not advised, really. lol I can only think of a one situation where you would normally use negative space. When it's commonly used to check that positive space stuff is positioned correctly. And that's about it. lol Starting off a painting with negative space is almost bound to create problems though. Very few people have the chops to accurately paint where negative space is without some kind of a sketch or preparation first. Sketch before anything, I say. lol Anyway, those are my thoughts on your question.