Is there a reliable way to determine when you should run DBCC CLEANTABLE to reclaim space?
The solution I'd think of for this problem is to run weekly a job that will run sp_spaceused for all tables in a database and save this data in a table. If there are differences in size for each table greater than..let's say..10%, I would run the dbcc cleantable.

My code to loop through table sizes looks like that:

if OBJECT_ID ('tempdb.dbo.#temp') is not null
    drop table #temp;

if OBJECT_ID ('dbo.BigTables') is not null
    drop table dbo.BigTables;
go

CREATE TABLE [dbo].[BigTables] (
    [table_name] [sysname] NOT NULL,
    [row_count] [int] NULL,
    [col_count] [int] NULL,
    [data_size] [varchar](50) NULL,
    [Date] [datetime] NOT NULL,
    [DBName] [nvarchar](128) NULL
);
GO

CREATE TABLE #temp (
    table_name sysname ,
    row_count int,
    reserved_size varchar(50),
    data_size varchar(50),
    index_size varchar(50),
    unused_size varchar(50)
);
go

INSERT     #temp
EXEC       sp_msforeachtable 'sp_spaceused ''?'''

insert into dbo.BigTables
SELECT     a.table_name,
           a.row_count,
           count(*) as col_count,
           a.data_size,
           getdate() as [Date],
    'MY DB' as DBName
FROM       #temp a
INNER JOIN information_schema.columns b
           ON a.table_name collate database_default
                = b.table_name collate database_default
GROUP BY   a.table_name, a.row_count, a.data_size
ORDER BY   CAST(Replace(a.data_size, ' KB', '') as integer) desc

DROP TABLE #temp;

Select * from dbo.BigTables;


Now you only need to build the logic that will verify what would be the size change through the week and schedule it.