MILES: Oh, you’ve taken out two previous loans on this house?
LORELAI: Um, yes.
This explains the difficulties Lorelai has been having in getting a loan – she has already taken two previous loans against her house, and is presumably in the process of paying them back (maybe cut down on the junk food buying?).
It doesn’t explain how she got turned down by a loan shark (fictionalised by Lorelai as Jacko’s Loans and Stuff), as the more desperate and in trouble you are, the more likely they are to loan you money at an exorbitant rate to make you suffer even more. I’d like to think Lorelai herself turned down the loan shark, knowing it was financially irresponsible.