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Hello again expat friends!
With all of your invaluable assistance, I've cast my search further afield (and consulted my doctor here in Singapore) and turns out that the university hospital in Chiang Mai offers the ability to treat my condition and the housing market is much slower there. I've found a lovely property with an owner willing to rent on a short term contract.

Now I've got Visa questions... The submission requirements to the Singapore embassy for a METV are as follows:

Passport: valid for no less than 6 months
Travel tickets in and out of Thailand with period of stay in Thailand not more than 60 days
For Multiple-Entry Tourist Visa: travel itinerary for the next 6 months for consideration
Evidence of adequate finance: an original bank saving statement which states bank contact information and deposit with the equivalent amount of not less than 8,000 SGD per person (6 months for financial statement)
Evidence of accommodation booking: proof of accommodation booking for the entire duration of the stay in Thailand or Invitation letter from an inviter in Thailand with a copy of IC card or Passport.
Singapore’s Long-term pass: If applicable, a copy of the applicant’s long-term pass
A letter explaining why they would like a multi-entry tourist visa

My questions are as follows:
Is the visa good for 6 months in Thailand in blocks of 60 days only, or 6 months total no matter how many times you leave and re-enter? i.e. could I spend 6 months in Thailand but leave and re-enter every 30 days?
If I intend to apply for an extension for 90 days, does this mean I need to book tickets that I'm able to cancel or reschedule? Or can I request/apply for the extension as part of the METV?
How strictly do I need to stick to the itinerary that I submit to the embassy? If my travel plans change, will I be denied re-entry because I've travelled on different days from what was submitted in order to get the METV? (i.e. if I submit to only travel once every 60 days but then decide to take an additional trip at the 30 day mark, or if my travel dates are brought forward by a day or two)
The owner was willing to sign a lease for 3 months with the option to renew for an additional 3 months. If I submit the 3 month lease and explain this, will the embassy take this as proof of accommodation or do I need to get a letter to accompany this?
What sort of rationale/justifications are typically approved for METV?
I am planning on flying out on 31 August and would like to get the visa approved ASAP so that I'm not stressing out about it, but I read somewhere that the 6 month validity is from the date of issue, so if I get it approved now, does that shorten the time I'm able to spend in Thailand?

Thanks!
-@Asyrol

Are you talking about a 60 days ME Tourist visa in Thailand? If so, you must apply abroad at an embassy or consulate. After 60 days counting from  the date of arrival,you must leave the country,but you can of course leave earlier. It's valid for 6 months. You can't apply for a 90 days extension, only for another 30 days if you're on a 60 days single entry visa. A 90 days extension doesn't exist.

I didn't know you need to follow a itinerary when applying for the 60 days ME Tourist visa.This wasn't a requirement earlier,but requirements differ between countries. In some countries you need to be employed (or self-employed) and the employer must send a reference to the embassy/consulate. You need to check out the specifics at the embassy where you are applying for the visa.

Hello!

Yes I'm talking about the 60 day ME Tourist Visa. I will be applying in Singapore and the requirements/guidelines listed above is what I've received from them. 

Sorry if I was unclear about 90 days - I meant to extend by 30 days to stay for a total of 90 days.

Hello!
Yes I'm talking about the 60 day ME Tourist Visa. I will be applying in Singapore and the requirements/guidelines listed above is what I've received from them.

Sorry if I was unclear about 90 days - I meant to extend by 30 days to stay for a total of 90 days.
-@Asyrol

You can't extend a 60 days ME Tourist visa at the local immigration office. You must leave the country and return. That's the whole point with an ME visa. You can always do a border run. From Bangkok you'll go to Burma (via the border crossing in Kanchanaburi). From Pattaya/Jomtien you'll go to Cambodia.

I was under the impression that you could extend the 60 days by an additional 30 each time. I've read that in total you can actually ends up stretching the 6 months to 9 months. My understanding that was 90 x 90 x 90 but are you telling me that's 60 x 30 x 60 x 30 x 60 x 30?

I was under the impression that you could extend the 60 days by an additional 30 each time. I've read that in total you can actually ends up stretching the 6 months to 9 months. My understanding that was 90 x 90 x 90 but are you telling me that's 60 x 30 x 60 x 30 x 60 x 30?
-@Asyrol

There's never been a 90+90+90 days. You're confusing the ME Tourist visa with the Single Entry visa. With the ME visa you must leave the country and return. With the 60 days SE you can do 60+30+30+30+30+30. It includes two border runs. This is not difficult to understand.

The information that I've found about METV is as follows:

Issued on the basis of tourism.

Valid to enter Thailand for 6 months from the date of issue.

Permits a stay of 60 days on each entry.

Allows multiple entries (using border hops) of 60 days during the validity of the visa.

The permit of stay can be extended one time on each entry for a further 30 days, and an additional 60 days for visiting Thai family/spouse.

To maximise the period of stay, if you make a border hop on, or just before the expiry (enter before date) of the Visa, you will be granted a a further stay of 60 days, which can again be extended one time for a further 30 days and an additional 60 days to visit Thai family/spouse.

You can stay for almost 9 months, or 11 months with an additional 60 day extension for visiting Thai family/spouse from a METV.

Furthermore, the visa extension website where you apply for your visa extension indicates that you're supposed to apply while you have less than 45 days left on your current visa, but while the visa is still active - *not* that you're supposed to leave and apply from outside of the country

The information that I've found about METV is as follows:
Issued on the basis of tourism.
Valid to enter Thailand for 6 months from the date of issue.
Permits a stay of 60 days on each entry.
Allows multiple entries (using border hops) of 60 days during the validity of the visa.
The permit of stay can be extended one time on each entry for a further 30 days, and an additional 60 days for visiting Thai family/spouse.
To maximise the period of stay, if you make a border hop on, or just before the expiry (enter before date) of the Visa, you will be granted a a further stay of 60 days, which can again be extended one time for a further 30 days and an additional 60 days to visit Thai family/spouse.
You can stay for almost 9 months, or 11 months with an additional 60 day extension for visiting Thai family/spouse from a METV.
-@Asyrol

If you have a 60 days ME Tourist visa you'll always get another 60 days when returning. The option to extend the 60 days another 30 days at immigration doesn't exist where I come from. If it does in Singapore then it's very strange because that's not the way a 60 days ME Tourist visa is designed to work in the first place. I also don't understand why you ask questions about it if you have read this at The Thai Embassy website in Singapore.

We've gotten incredibly side-tracked on the 30 day extension which was only a part of one of my questions - all of my other questions remain un-answered and I have not been able to find any questions on the thai embassy website or elsewhere online, hence why I was hoping to get some insight here.

We've gotten incredibly side-tracked on the 30 day extension which was only a part of one of my questions - all of my other questions remain un-answered and I have not been able to find any questions on the thai embassy website or elsewhere online, hence why I was hoping to get some insight here.
-@Asyrol

How hard it is to check out the requirements and info about visas at the Thai embassy in Singapore? I just did and the 60 days ME Tourist visa doesn't exist,just the 60 days Single Entry. Then it will work like this: 60 days TR visa + a 30 days extension at the local immigration office,a border run will give you another 30 days,then another 30 days at the local immigration office, another border run for 30 days and the last extension at the immigration office. So: 60+30+30+30+30+30 days. You can only do 2 border runs per calendar year.

See this link:

Furthermore, the visa extension website where you apply for your visa extension indicates that you're supposed to apply while you have less than 45 days left on your current visa, but while the visa is still active - *not* that you're supposed to leave and apply from outside of the country
-@Asyrol

You can apply for the extension 45 days before the visa expires until the last day. BUT, don't extend it that late. If your papers aren't in order you're on overstay if you don't leave before the visa expires. Do it 1-2 weeks before it expires. This is so easy to understand but you're overthinking it.

To be clear, yes there is the 6 month multi entry visa, it's on the Singapore website under tourist visa

Just ignore the question about the 30 extension. As I said, we seem to be getting side tracked here.

As you can see from the requirements that I listed in my original questions they ask for an itinerary for the full 6 months. How closely do they track that? If I say that I'm going to fly to Vietnam from the 4th to the 10th and change my mind and fly to Cambodia from the 3rd to the 7th an I going to be denied re-entry because my travel doesn't match the itinerary I submitted?

Will my 3 month lease and a note suffice or do I need a letter from my landlord?

Have you ever seen this request for a reason for the visa before? Any idea what constitutes a sufficiently good reason?

Should I apply now, or wait a couple of weeks?

To be clear, yes there is the 6 month multi entry visa, it's on the Singapore website under tourist visa
Just ignore the question about the 30 extension. As I said, we seem to be getting side tracked here.

As you can see from the requirements that I listed in my original questions they ask for an itinerary for the full 6 months. How closely do they track that? If I say that I'm going to fly to Vietnam from the 4th to the 10th and change my mind and fly to Cambodia from the 3rd to the 7th an I going to be denied re-entry because my travel doesn't match the itinerary I submitted?

Will my 3 month lease and a note suffice or do I need a letter from my landlord?

Have you ever seen this request for a reason for the visa before? Any idea what constitutes a sufficiently good reason?

Should I apply now, or wait a couple of weeks?
-@Asyrol

Your itinerary isn't important, you can just mention some places you want to visit. Immigration in Thailand will know nothing about it. It's not connected to thai embassies what so ever. Immigration won't know what you have written in your application. Your 3 months lease should suffice. Apply now and see what happens.