Conditional: IF current author’s custom post has a post thumbnail

Try this

<?php
if ( 
1 < count_user_posts( get_current_user_id(), "CUSTPOSTTYPE" ) 
&& is_user_logged_in() 
&& has_post_thumbnail()
) {
?>

// if(TRUE,TRUE,TRUE)

to debug, you should check the output of the following…

var_dump(count_user_posts( get_current_user_id(), "CUSTPOSTTYPE" ));
var_dump(is_user_logged_in());
var_dump(has_post_thumbnail());