Hi Sag Moon,
You'll find that, the more proficient you become at horary, the less you find 'yes/no' questions, which are sort of crude renderings of very elegant charts, like trying to make the Mona Lisa into a stick figure coloured with crayons. After a manner of speaking, there is no such thing as a simple 'yes/no' chart, although beginners start off reading them that way.
It's not as simple as looking only at angles or chart rulers; much as most good horary questions are not 'simple' questions but are influenced by everything else in the querent's life. So for example, your 'work' question is not just about one career or the other, but will also involve the querent's dissatisfaction with one, or his/her lack of money and therefore a need to improve finances, or indecision about 'what they want to do', etc. In other words, there is *always* a reason and a background to why the querent asks a question, and it is up to the astrologer to get this information *first*.
'Would it be wise' is a very relative term: what is 'wise'? And wise for whom? And in what manner the 'wisdom'? Financial? Emotional? Practical?
This is why it is very important to get *as much background information as possible* from the querent before embarking on a reading of the chart.
To get a definitive answer in horary requires a few 'rules':
1. That all or most of the considerations before judgement are met, especially the condition of the Moon noted.
2. That the rulers of the question (the querent and quesited) are clearly defined *before* you try to read the chart.
3. That the question is *clearly* understood by the astrologer, with background information provided.
In other words, you not only look at the angles, but first and foremost the Moon and her condition; the significators of the players, and their condition; the relationship of the players to one another (trine? square? applying? separating?) and THEN you look at the angles. From all of this, it is very easy to get not only what 'The Answer' is, but also the reasons *why* the querent is asking, what they hope for out of the question, and what the outcome is likely to be should they continue along the same path.
Sorry to go on at such length about it, but I always feel a certain amount of alarm when attempts are made to reduce horary to one simple equation!
Horary charts *can* give 'yes/no' answers, but you'll find, the deeper you dig, the deeper and more comprehensive your answer will be, and the more satisfied your client will be. Querents very seldom just want 'yes/no' answers; they want the 'whys and wherefores' as well.