Passport history of what the I/O deems excess of entries via combination of previous Tourist Visas and Exempt Entries that in the judgment of the I/O indicates possibly working (no specific rule or number needed). I know of 30 day Extension applications being turned into 7 days to Exit Thailand. Not common place - but can happen.
If your passport is NOT filled with back to back tourist Visas and / or Exempt Entries Krabi will be fine - easy. But in recent months Krabi has been rejecting people whose passport is as I just described
Depending on where you are departing from - just to do a turn around inside an airport (passing through immigration and back through) - then Kuala Lumpur might be better. I've done this at KL - a long walk but easy enough. Booking two one way tickets may get you better times.
Ah - consistency from one Imm office to another. What I wrote applies for Krabi and I believe in, some other outlying Imm Offices. And when applying for the Non O 90 day in Penang then doing the one year Extension of Stay in Krabi. They want to see the original of the Embassy Affidavit in both places. A friend went through this sequence just a few months ago - Penang then Krabi and verified what I thought I knew. By the way if I rememberd to ask I've never been refused to get back an original document in an application procedure as long as I had a good copy to hand to them., i.e. Rental / Lease Agreement and the Income Affidavit was examples.
Note: The second option Tod listed to meet the financial requirements to apply for a Non Immigrant O Visa is the Income Method. You just need to have monthly income from outside Thailand - usually one's home country. Then go to your own country's Embassy in Bkk - sign an Income Affidavit (Embassy Letter) swearing that you gave this income. For Americans there is no proof required - just the sworn statement. To get this Form go to the American Embassy website (consular services I think) Make an Appointment on line and download the affidavit form (it can be filled in on line). Fill it out but don't sign it until on the presence of the Embassy officer. It cost $50 or Thai Baht Equivalent. The website tells you what they consider the exchange rate to be for the fee. You state your income in US Dollars. With the Dollar losing ground lately against the Baht it is best to wait until you are at the Emassy to fill that it. And Best to stare a monthly income amount in your favor against future exchange loses as the form is good for 6 months. You include this raised seal stamped Income Affidavit in your Non Imm O application. Don't add proof documents - the Affidavit is enough. When applying for the Non O 90 days take the original but don't let them keep it because you need it to apply for the one year Extension of Stay which will come up 45 days or so after getting the Non O awarded.