What is the wind in this context?

Solution 1:

In the second occurrence: "Maybe if I'm really lucky such tricks could put me net ahead. But the wind is there, no question*", wind = risk or danger.

This use is uncommon but appropriate here because the writer is extending the metaphor of sailing close to the wind. He is explaining that his "hack" (= method of solving a problem) does have some risks/dangers/possibilities of going wrong, etc.

Solution 2:

Sailing close to the wind.

To understand this metaphor, you really have to understand the basics of sailing.

No boat can sail directly into the wind. So if your direction is in the way from which the wind is coming, you need to "tack" - i.e. sail from side to side in order to make progress.

The narrower the tacks you take, the faster you complete the course. That means "sailing close to the wind", not directly up-wind but close to it. You need to keep the sheets (sails) close-hauled, and (in a small dinghy) move your own weight to the other side to prevent capsizing.

But if you do not quite get it right, and a gust of wind arrives from the other direction, the boom can crash over and potentially knock you overboard. Certainly your weight will be wrongly positioned.

I have never sailed a large boat but I assume the same principle applies.

That is why, unless you are very experienced, it is inadvisable to "sail close to the wind".