As an art collector, you basically have 2 objectives. The first is as a form of investment while the second is all about passion and interest. If you are buying art for investment then you will surely want to have every cents worth of it, meaning that you will want to buy a piece of work at the lowest price possible and then selling them at a much higher price in the future. If you are in the latter group, then the price is not really an issue as you believe that there is no price tag for good art and you will buy if you can afford it.
Where then can you buy your art? The most common places to do so would be at the galleries and this is where you will be aware that they usually take a share in the price of the art you are buying. So your other option is to try to buy directly from the artists themselves. This is easier said than done because established artists are usually engaged by a gallery.
So what should you do? Be aware that the artists who are represented by a gallery would try not to sell their art directly to you because they do not want to undercut their paymasters.
The most important thing that you must remember when discussing with the artist is that what you are trying to achieve is a win-win situation for everyone which includes yourself, the artist and the gallery.
For artists who are engaged to a gallery, you must be a bit more tactful.
You must be too pushy. If you can go official through the gallery, it would be good but if you think that the gallery might impose prices which are too exorbitant, then the artist would be the first person to talk to. Tell them that you will be approaching the gallery after that discussion where you can tell the artist what you want. If the artist insist that the discussion of dollars and cents be left with the gallery, so be it. You can make your offer, but make it subtly.
Another way is to attend group shows at galleries where you can identify new artists who are emerging and would most likely be trying to sell their art. These are the ones who are still trying to establish their art in the scene and they would mostly welcome anyone who likes their body of work. Their art would be more affordable and at the same time, they are more willing to sell to you directly. Always conduct your own research prior to approaching the artist and learn more about their background and history.
Never start a conversation with an artist of a possible commission work. You should talk about their art and which one interests you most. They might have similar pieces along the same series which you might be interested to buy. Ultimately, if the artist is not represented they will be more than willing to sell to you but if they are, then you must assure them that you will be in contact with the gallery. If a price is agreed, the artist will inform the gallery about it.