John F Chandler Yeah, the key is to notify your bank that your "slow traveling abroad." Telling them you're "moving" or "living" there is not recommended.

John F Chandler This shouldn't be an issue, as long as you maintain a valid US address.

Even if it's your first trip to the Kingdom, immigration doesn't care what your circumstances are for not properly planning ahead. Yes, if you apply for another extension, it will get denied. Whatever you do, do not overstay! Your next attempted entry will almost certainly be denied by immigration. If you plan to return and stay longer on your next visit, I highly recommend applying for a proper tourist visa like the METV (up to 180 days) or DTV (up to 5 years).