If it were possible to add $11$ tiles so that no more could be added (this is called a clumsy packing, by the way), then the leftover holes would consist of $14$ isolated $1\times 1$ cells.
From each of these $14$ squares, place a counter on the four squares adjacent to it, which will either be on already-placed dominoes or will lie outside the border of the chessboard. But it is easy to see that a domino can't be next to more than $4$ of these holes, or else two of them would be adjacent (which we have assumed is not the case). So of the $14\cdot4=56$ counters placed, at most $44$ of them can fall on dominoes. This leaves $12$ counters to lie on the border of our $6\times 6$ chessboard, each of which must originate from a hole on the corresponding edge of the chessboard. But note that if we have more than $4$ holes on any given edge of the chessboard, two of them must be adjacent, so by the pigeonhole principle, every side must have exactly $3$ holes on it.
This means that up to rotation, the board must look like this:
O _ O _ O _
_ ? ? ? ? O
O ? ? ? ? _
_ ? ? ? ? O
O ? ? ? ? _
_ O _ O _ O
where a _ indicates one of the $14$ holes, and an O indicates a cell where a domino has been placed. But then we have identified a corner cell that is occupied by a domino, and yet has no neighbors for its other half to lie in. This is a contradiction.
(As an alternate method of proof, you could convince yourself that at least one domino must have $3$ or fewer counters on it, in which case you could more readily obtain a contradiction along one of the sides of the chessboard. This isn't too hard to do either.)
A paper analyzing this question for $n\times n$ boards is here, and proves that it takes $n^2/3$ dominoes for a clumsy packing when $3|n$. The number of dominoes in a clumsy packing is given at A280984 in the OEIS.
As to the question at the end of your post, I don't think fault-free domino tilings are particularly related to this problem.