Best way to get gobs of cash

The up front cash for apartment is one good reason to visit a commercial bank (most of the big names are "commercial" banks) and order Euros up front. Most banks have some euros on hand but you might have to order and wait a couple of days. Alternatively, you can open several travel accounts, each with it's own debit card. Use the daily limit on each to get the cash you need - then keep the spares in your moneybelt in case you end up needing them. USAA has free checking (don't have to be military) with a $600 a day limit and only a 1 percent fee for each transaction. I use them as my primary travel debit card now.

Yes, you will get totally screwed with trav checks. Is there a possibility of a wire transfer?

Could you just order Euros from your bank and specify a large denomination - like 500 Euro bills. You could tell your apartment owner or agent that you'll be paying in large bills and clear it up front. They wont take up much room in your money belt....

If the apartment owners will accept bank drafts in euros, open an account with XE Trade. Money will be taken from your checking account by electronic transfer and bank drafts will be made payable to the owners. The exchange rate will be only slightly higher than the international rate on the day each transaction is inititated. There are no fees. Have the drafts mailed to your home rather than to the owners. Hand them over when you arrive at each point. If you don't mind paying in advance, XE Trade also will transfer the money directly into each owner's bank account at no extra charge. Or they'll do wire transfers, but there is a charge for those.

You don't say what country you are going to but be aware, that cashing Travelers Checks in Germany at banks is impossible. They stopped cashing them several years ago. Only place you can cash them in Germany are the money exchanges located at the airports and big train stations. I would forget the travelers checks completely.

K.N. ATMs (bancomats) are the easiest and cheapest way to get euro. Check with your bank to verify your limit is high enough to cover the amount you want, if not, ask them to raise the limit. On joint accounts sometimes the limit is per card not account so two cards could each take out the limit on the same account. Open another account to increase the amount you can withdraw. It is also a good idea for a backup. Look for the best deal for this new travel account. See http://flyerguide.com/wiki/index.php/Credit/Debit/ATM_Cards_and_Foreign_Exchange You want a low(or Zero) foreign transaction fee and a low or zero charge for out of network fees. Italian banks will not charge you for using their bancomats. On the back of your ATM or debit card you need a Visa - Plus or MasterCard - Cirrus symbol. The Italian bank ATM may have a transaction limit (the amount you can pull out at one time), usually between 250 and 500 euro, but you can perform multiple transactions until you reach your bank's daily limit.
When you get there ask your apartment owner where is the nearest bancomat? The owner will probably walk you to it so you will not be carrying a lot of cash long.

And remember that in Europe they use decimals where we use commas in numbers, and vice versa. I remember trying to withdraw from an ATM at the Rome airport, and having my transaction declined for not enough funds. Took a while to figure out that my request for 400.000 Euros mean 400,000.

I talked with my bank before I went to Europe last year and raised the amount I could withdraw at one time. It worked very well and wasn't any trouble to do.