Ryan, providing that you have the necessary paperwork and the funds in the bank two months prior to your application, it is actually quite easy to do. Sometimes the immigration may ask you to bring additional paperwork. Always carry all possible paperwork with you with double copies and originals as much as possible.
In my area it is required to do every time I return from overseas. It is a simple form, anyone can fill it in. Make sure the landlord has a copy of the deed and the copy of their ID. It takes 10 minutes. You don't need to pay anyone. It needs to be done immediately after your arrival or the next day. Or you will be fined per day you are late. I think submitting TM30 costs 100 Baht at the immigration office. It is actually the landlord's duty to submit the TM30 to tell the immigration that someone staying at that address. So in theory the landlord should pay for it.
Most medicine are available without prescription in Thailand. If it is a problem you can go to a doctor or hospital where they will give you the medicine and prescription. I had to go to a private hospital for a consultation that cost me about £15 including the medicine. Hospital stock medicine and sell.
If you are in Thailand with the correct paper work and 800K in a Thai bank you can get it the same day of your application. At least that is my experience. My on line visa application in the UK took 2 days 3 years ago.
I was looking into this and found one company in Australia, called "Medical Travel Shield". They appear to say that they cover certain medical conditions. I don't know this company so please don't quote me on that or take my word as true, but you could speak to them and find out what they say. And sometimes they guide you to the company that may help you. I wish you a good health and good luck.
I worked in insurance for over 25 years. In principle, insurance provides safety for unexpected events and emergencies. Anything that is known to happen will not be considered under most insurance policies, unless it is declared and accepted. In your situation, you are going to Thailand with the intention of having treatment for a known condition. I would say it will be quite difficult for most insurance companies to provide cover for it. There are policies that may cover events like that but they are generally corporate policies to cover employees of big corporations. Or you may find a policy that may cover your treatment with a very high premium. Insurance is based on utmost good faith principle so anything you know that is relevant, has to be declared. Then the insurance company will decide whether or not they should accept the risk, but in your case it is no longer a risk, it is an event that is known to happen. Although you might think it is not a pre-existing condition, it is something you are travelling to Thailand with the intention of receiving treatment. Having said that all, there are private medical insurance policies that may provide cover for elective surgeries/treatment. It is just a matter of finding the one that does that.