TextWrap and Anchored Objects

Okay, I've been using InDesign since it was PageMaker 4.3 so I'm pretty familiar with the features and the intents behind them. Lately I've had a problem for which I can't seem to find a fully acceptable work-around. It involves text-wrapping anchored objects within a large, multi page flow of text.
Boiled down to a basic description of the issue, I need a graphic to appear on a page within a text block at a certain point, that is, at the top of a justified paragraph on the extreme right side of the column. The object occupies 7 lines of text, dropping down into the paragraph from line 1. The object needs to have a word wrap applied causing the text within the block to flow around it.
The problem is that as the document evolves, the quantity of text that precedes the paragraph holding the graphic changes. As text is added to preceding paragraphs, text advances through the text blocks to a point where the graphic now begins to be displayed beyond the bottom of the text block rather than jump to the next text block. Forcing the object to stay within the text block (by using the "Keep with top/bottom column boundaries") pushes the object up, effectively leaving the original location and invading the preceding paragraph.
The first solution I tried was to anchor the object 7 lines deep in the paragraph, then manually move it up to the first line using the "Y-offset" in the "Anchored Objects Options" palette. When I do this, the object's text wrap fails (!), always working only at line 7 and below and not moving up with the object.
My current solution is to not embed the object inline at all, but place it over the text block. This works but is unsatisfactory since the text is constantly changing, forcing me to stop and reposition the graphic - plus the 500 or so similar objects that follow in similar situations further along in the document.
Any ideas?

Unfortunately, no. If the anchor is inserted at the top of the paragraph (where I want the top of the image to be), the image won't flow to the next text block when any other part of the image (i.e., any part of the image that is not on the first line where the anchor is) is beyond the end of its text block.
Here is how I want the page to look:
Here, the graphic is not placed inline but sits over the text with textwrap set.
But rather than have all my objects placed over text, I want them inline. If I place the anchor anywhere below the first line of text, (again, the line where I want the top of the image to be), text wrap won't function above the anchor point regardless of how high I move the image:
If I place the graphic in its own paragraph above the first line of the paragraph, the result works well as long as the text preceding the anchor doesn't flow any further (i.e., no additional text is added). But as text is added and once the line holding the bottom of the photo flows to a new text block, one of two problems arises. If "Keep Within Top/Bottom Column Boundaries" is checked the graphic moves up:
If "Keep Within Top/Bottom Column Boundaries" is unchecked, the graphic begins to bleed out of the text box:
I can't believe there isn't a simple (or even complex) solution to this problem...

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