I think this can be done after all. What you want to do in your single article template is to call the latest issue, pull up all the articles related to it, then try and match it to the current article you are looking at. If you get a match, then the article is in the latest issue.
Note, in your case: Articles = The Playa Parents and Issues = The Playa Children. Seem backwards, but the Article entries have the Playa field and so are the parents.
You would put this in your single article template:
<!-- get latest issue (playa children) -->
{exp:channel:entries channel="issues" orderby="date" sort="desc" limit="1"}
<!-- get articles of the issue (playa parents) -->
{exp:playa:parents channel="articles"}
<!-- try and match entry_id of article with the entry_id of an article in the latest issue -->
<!-- segment_x is the segment in your URL that hold the current articles entry_id -->
{exp:ifelse parse="inward"}
{if entry_id == "{segment_x}"}
This article is in the latest issue.
{if:else}
Something else…
{/if}
{/exp:ifelse}
{/exp:playa:parents}
{/exp:channel:entries}
Give it a whirl. I’m not sure if I have the code right, but it should be possible. You may need the Playa coparent tag instead of the parent tag. Not sure.
Note: I am using the free Mark Croxton IfElse plugin that makes IfElse statements more efficient.