diff --git a/org_mode_samples/greater_element/plain_list/checkbox.org b/org_mode_samples/greater_element/plain_list/checkbox.org
new file mode 100644
index 00000000..e987168d
--- /dev/null
+++ b/org_mode_samples/greater_element/plain_list/checkbox.org
@@ -0,0 +1,3 @@
+- [ ] Foo
+- [-] Bar
+- [X] Baz
diff --git a/src/compare/diff.rs b/src/compare/diff.rs
index f37c5963..0a58bb77 100644
--- a/src/compare/diff.rs
+++ b/src/compare/diff.rs
@@ -83,8 +83,6 @@ use crate::types::Paragraph;
 use crate::types::PlainLink;
 use crate::types::PlainList;
 use crate::types::PlainListItem;
-use crate::types::PlainListItemCounter;
-use crate::types::PlainListItemPreBlank;
 use crate::types::PlainListType;
 use crate::types::PlainText;
 use crate::types::Planning;
@@ -1121,108 +1119,70 @@ fn compare_plain_list_item<'b, 's>(
     source: &'s str,
     emacs: &'b Token<'s>,
     rust: &'b PlainListItem<'s>,
-) -> Result<DiffEntry<'b, 's>, Box<dyn std::error::Error>> {
-    let children = emacs.as_list()?;
-    let mut child_status = Vec::new();
+) -> Result<DiffEntry<'b, 's>, Box<dyn std::error::Error + 's>> {
     let mut this_status = DiffStatus::Good;
+    let mut child_status = Vec::new();
     let mut message = None;
 
-    // Compare tag
-    let tag = get_property(emacs, ":tag")?;
-    match (tag, rust.tag.is_empty()) {
-        (None, true) => {}
-        (None, false) | (Some(_), true) => {
-            this_status = DiffStatus::Bad;
-            message = Some("Mismatched tags".to_owned());
-        }
-        (Some(tag), false) => {
-            let tag_status = tag
-                .as_list()?
-                .iter()
-                .zip(rust.tag.iter())
-                .map(|(emacs_child, rust_child)| {
-                    compare_ast_node(source, emacs_child, rust_child.into())
-                })
-                .collect::<Result<Vec<_>, _>>()?;
-            child_status.push(artificial_diff_scope("tag", tag_status)?);
-        }
-    };
+    compare_children(
+        source,
+        emacs,
+        &rust.children,
+        &mut child_status,
+        &mut this_status,
+        &mut message,
+    )?;
 
-    // Compare contents
-    let contents_status = children
-        .iter()
-        .skip(2)
-        .zip(rust.children.iter())
-        .map(|(emacs_child, rust_child)| compare_ast_node(source, emacs_child, rust_child.into()))
-        .collect::<Result<Vec<_>, _>>()?;
-    child_status.push(artificial_diff_scope("contents", contents_status)?);
-
-    // Compare bullet
-    let bullet = get_property_quoted_string(emacs, ":bullet")?
-        .ok_or("Plain list items must have a :bullet.")?;
-    if bullet != rust.bullet {
-        this_status = DiffStatus::Bad;
-        message = Some(format!(
-            "Bullet mismatch (emacs != rust) {:?} != {:?}",
-            bullet, rust.bullet
-        ));
-    }
-
-    // Compare counter
-    let counter = get_property_unquoted_atom(emacs, ":counter")?;
-    let counter: Option<PlainListItemCounter> = counter
-        .map(|val| val.parse())
-        .map_or(Ok(None), |r| r.map(Some))?;
-    match (counter, rust.counter) {
-        (None, None) => {}
-        (None, Some(_)) | (Some(_), None) => {
-            this_status = DiffStatus::Bad;
-            message = Some(format!(
-                "Counter mismatch (emacs != rust) {:?} != {:?}",
-                counter, rust.counter
-            ));
+    for diff in compare_properties!(
+        source,
+        emacs,
+        rust,
+        (
+            EmacsField::Required(":tag"),
+            |r| if r.tag.is_empty() {
+                None
+            } else {
+                Some(r.tag.iter())
+            },
+            compare_property_list_of_ast_nodes
+        ),
+        (
+            EmacsField::Required(":bullet"),
+            |r| Some(r.bullet),
+            compare_property_quoted_string
+        ),
+        (
+            EmacsField::Required(":counter"),
+            |r| r.counter,
+            compare_property_numeric
+        ),
+        (
+            EmacsField::Required(":checkbox"),
+            |r| r
+                .checkbox
+                .as_ref()
+                .map(|(checkbox_type, _)| checkbox_type)
+                .map(|checkbox_type| match checkbox_type {
+                    CheckboxType::On => "on",
+                    CheckboxType::Trans => "trans",
+                    CheckboxType::Off => "off",
+                }),
+            compare_property_unquoted_atom
+        ),
+        (
+            EmacsField::Required(":pre-blank"),
+            |r| Some(r.pre_blank),
+            compare_property_numeric
+        )
+    ) {
+        match diff {
+            ComparePropertiesResult::NoChange => {}
+            ComparePropertiesResult::SelfChange(new_status, new_message) => {
+                this_status = new_status;
+                message = new_message
+            }
+            ComparePropertiesResult::DiffEntry(diff_entry) => child_status.push(diff_entry),
         }
-        (Some(e), Some(r)) if e != r => {
-            this_status = DiffStatus::Bad;
-            message = Some(format!(
-                "Counter mismatch (emacs != rust) {:?} != {:?}",
-                counter, rust.counter
-            ));
-        }
-        (Some(_), Some(_)) => {}
-    };
-
-    // Compare checkbox
-    let checkbox = get_property(emacs, ":checkbox")?
-        .map(Token::as_atom)
-        .map_or(Ok(None), |r| r.map(Some))?
-        .unwrap_or("nil");
-    match (checkbox, &rust.checkbox) {
-        ("nil", None) => {}
-        ("off", Some((CheckboxType::Off, _))) => {}
-        ("trans", Some((CheckboxType::Trans, _))) => {}
-        ("on", Some((CheckboxType::On, _))) => {}
-        _ => {
-            this_status = DiffStatus::Bad;
-            message = Some(format!(
-                "Checkbox mismatch (emacs != rust) {:?} != {:?}",
-                checkbox, rust.checkbox
-            ));
-        }
-    };
-
-    // Compare pre-blank
-    // :pre-blank appears to count the line breaks between "::" and the contents in a descriptive list. Oddly enough it does not count the spaces so I'm not quite sure what the value is.
-    let pre_blank = get_property_unquoted_atom(emacs, ":pre-blank")?;
-    let pre_blank: Option<PlainListItemPreBlank> = pre_blank
-        .map(|val| val.parse())
-        .map_or(Ok(None), |r| r.map(Some))?;
-    if pre_blank.unwrap_or(0) != rust.pre_blank {
-        this_status = DiffStatus::Bad;
-        message = Some(format!(
-            "Pre-blank mismatch (emacs != rust) {:?} != {:?}",
-            pre_blank, rust.pre_blank
-        ));
     }
 
     Ok(DiffResult {