Certain MultiPolygons cause “BOOM! Could not generate outside point!” in PostGIS?

Sounds like your using geometry rather than geography tables

In order to load geometry data into a geography table, the geometry first needs to be projected into EPSG:4326 (longitude/latitude), then it needs to be changed into geography. The ST_Transform(geometry,srid) function converts coordinates to geographics and the Geography(geometry) function “casts” them from geometry to geography.

If your data is geographically compact (contained within a state, county or city), use the geometry type with a cartesian projection that makes sense with your data. See the http://spatialreference.org site and type in the name of your region for a selection of possible reference systems.

If, on the other hand, you need to measure distance with a dataset that is geographically dispersed (covering much of the world), use the geography type.

to convert your geometry to geography use the code below

CREATE TABLE yourdata_geog AS
SELECT
  Geography(ST_Transform(the_geom,4326)) AS geog,
  attr1,
  att2
FROM yourdata;

http://postgis.net/workshops/postgis-intro/geography.html