Yes, tile on painted brick is probably a loser. Suggest you take a power sander with about 36 grit to it to cut off some of the paint and level roughness. Then set 1/2" Hardibacker in place with latex modified thinset and Tapcon screws into the mortar, particularly around the edges. Normally James Hardie recommends screws every 8" each direction. Make a point of getting the Hardibacker on flat; check with a straightedge.
Ditra is not used much here and I don't understand the reason for using it anywhere. My favorite tile store lady said dit-what? when I asked her about it, and she has been in the business for many years.
Size of the tile is your call. People are leaning toward larger tiles these days.
For more information about setting tile, visit my website at www.bobf.info.
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