Of the places you listed in your email, I have only been to Bangkok and Krabi (actually Ao Nang). I have spent some time in Chiang Mai but not Chiang Rai....your email said Rai but the post above says Mai, so I will include some info for Chiang Mai.
On the dollar amount that you mentioned for your budget for each country, was this including food, lodging, travel and touristy stuff too?
When we are in Bangkok, we tend to stay at the Indra Regent (USD $40). We have stayed in a few different hotels in Bangkok and this one seems to offer us what we want without costing too much. We usually book it online because you can get a bit cheaper rate including breakfast than if you do it directly with them. We use Hotelthailand.com to book hotels in Thailand. We have never had any problems with credit card fraud or bad stays using them. The hotel is located in a great area for us (shopping, lightrail, food, internet), and the customer service has always been really great. I highly recommend visiting the Grand Palace and Ayutthaya while you are in the area. We took the train to Ayutthaya (about an hour out of town) and it was great, and very cheap (about 23 baht) each way.
In Krabi (Ao Nang) we stayed at two different hotels that were really nice and not too much. When we visited there several years ago, these were 4 star resorts and we only paid USD $28 per night (they are a bit more now, with the exchange rate flucuation). Some feel this is a lot for hotels in Thailand but we aren't usually visiting on a shoestring budget and prefer to have AC and hot water in our room. The two places we stayed at in Ao Nang, were the Ao Nang Villa Resort and Ban Ao Nang Resort. You can book both of these through Hotelthailand.com as well. We enjoyed our stay in this region (we were there for some rock climbing), but this was long before the tsunami so I am not sure how hard they were hit and the results of that devastation.
In Chiang Mai we stayed at the Porn Ping Hotel. It is on a similar level with those in Krabi, and Bangkok. It is close to the night market, and several places to eat that are on the moat/river along with the restaurants in the hotel and the food court at the night market. We took a taxi up to the Wat Doi Suthep for about 200-300 baht round trip and explored it on our own instead of doing a tour. We made the mistake of taking one of the factory tours (while interesting, we had to put up with a lot of high pressure sales at a rug store). We took a small mini bus into the Golden Triangle on a day tour that was really interesting and fun. We flew into Chiang Mai from Bangkok on Thai Airways (they have a flight up there just about every hour each day), and took a taxi from the taxi stand outside to the hotel for about 100 baht.
As far as food goes, we are the kind of travelers that tend to steer away from most touristy things, and prefer to explore on our own (we have done a few small tours in regions that we can't get around on our own on). So we tend to eat at the small mom and pop places and avoid the big shows and expensive restaurants. It seems you get a better look at the culture that way. Usually these places are very economic and delicious but not fancy.
Hope this is helpful, and have fun on your travels. SE Asia is an amazing place.
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