booleans/planar?

Hi there, i think i have had my fair share of boolean operations difficulties, some of which i have been ABLE to resolve and no, this isnt the problem where the whole model dissapears, that only happens if i do a difference boolean operation and the object is not a solid such as a missing face on a cube for example, what i do have a problem is this, iam modelling orthanc (or trying) the tower of isengard from lord of the rings and iam at the first level or row of windows, difference booleans not such a problem, but the face of the tower is on a slant approximatly 4 degrees, when i do a boolean difference operation and try to render it maya simply locks up in the middle of an IPR, has happened 3 times .. then i tried viewing my tower using deep exploration, what i found was that faces around the the windows were all over the place here is the best i could do to show anyone who could help me with this problem

user added image

as you can see theres clearly something wrong or i might be that iam missing something, to add to my problem is iam actually doing this model for a game (yers i know polycount user added image

) first problems first i suppose, one thing i have found was that doing a difference boolean operation which leaves a hole in the middle of an object without any edge attached to a border edge leaves a triangle hole as though maya couldnt finish triangulating around the hole such as what iam trying to do on a surface, this applies to the above shown, i only an 12 week old in the world of modelling and if it wasnt for these types of problems i would say modelling is almost meditational user added image

i hope someone can help me out and thanks in advance

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