Left Join not returning all rows

You must place the pr7 criteria in the join, not in the where clause. The where clause works on the entire result set AFTER the join has been performed.

SELECT pr.*, pr7.value AS `room_price_high`
FROM `jos_hp_properties` pr
LEFT OUTER JOIN `jos_hp_properties2` pr7 ON pr7.property=pr.id and pr7.field=23

Sure. Move the WHERE condition to the JOIN:

SELECT pr.*, pr7.value AS `room_price_high`
  FROM `jos_hp_properties` pr
       LEFT JOIN `jos_hp_properties2` pr7 
       ON pr7.property=pr.id
   AND 
       pr7.field=23