Banks are kinda funny here, in my experience. Many times the bank customer must use the branch where they opened their account. Recently, I had to update my passport and I could only do that at the branch where I opened my account. I think this same is true for some/most/all immigration paperwork. Hence, your friend may want to open the bank account where they plan to settle.
I use agents frequently and recommend avoiding them if possible. They are great if you need them. Immigration can be a pain, it depends on where you are and the immigration office that serves the area. Agents make it easier but often times when you have a passport riddled with questionable visas, immigration will demand bribes (its an odd sort of demand).
However, in your situation, if you prefer to use the passive income method you will need to show 65K+ being deposited into a Thai bank account wholly controlled by you, over the course of a year. I suspect you do not have that requirement. Also, I believe the 800K method requires the money to be in the bank account for a couple of months before you apply for the visa.
You're best option may be to make a plan. Get a new tourist visa (or whatever), then execute your plan, and do whatever the next next time you need a visa
I would come, visa exempt, then when you are here work out your future plans. I have a buddy that has a retirement visa. He tells me its better to get those in-country because of insurance reasons... That may not apply to you, now, but I am quite sure you can get a retirement visa while you are here. If you have a few extra dollars and don't want to be bothered, you can hire a visa agent to do it for you..
They've told me that a couple of times. I suspect if you came back in now, they wouldn't tell you that a second time. You should have a proper visa but they're pretty flexible.
The contract isn't necessary unless you intend to do all the immigration stuff yourself.
The contract doesn't have to be anything fancy and can be in English. Find a simple 1 page rental agreement on the interweb, alter it to suite your needs, print sign date, both you and your friend. You will also need to attach copies of the chanute and blue book, copies of the data page from your passports (both of your passports) signed. I may not have all the requirements right, it's been a couple of years. My experience with immigration is that they ALWAYS ask for more paperwork, so be prepared for that.