The most important thing is to know what you actually want to do and your reasons for coming to Thailand. If working in a restaurant here isn't really an objective of yours, and would be more of a "would be nice if it happened" thing, and the primary goal is to just be in Thailand—and you can afford to just be in Thailand for five years (or less if you wanted, of course)—then a DTV would be fine. You don't really make this clear in your original post. The DTV is a great way to stay in Thailand for a long time, but you have to be able to afford to be here for that time under your own financial steam (not by working here).
Come on now, the DTV *IS* a long-term visa. Five years. The fact that holders of it have to leave and come back in every 180 days (360 with a simple extension) doesn't change the fact that overall, they can stay in the country for five years with it. Yes, the DTV is classified as a "tourist type" visa, but it is unique among tourist visas because you can stay for that long.
Because a DTV allows people to be in Thailand for FIVE years (with quick exits and re-entries, but that's minor). Would you want to live in Thailand for five years without being able to get a Thai bank account? No, you wouldn't.
Based solely on your FB profile picture (which I totally get the humor of), you might be a bit too nonconformist for Thailand, honestly. Or you might find Thai society a bit too conformist, would be another way of saying it. Are you ready to live in a place where quirky personality and severe originality aren't really appreciated? I came here (to live) with long hair and realized very quickly that between the climate and the fact that instead of identifying myself as an artist, musician, and free-thinker (which was my intent with it, because I am those)—a signal that gets read correctly in North America—to Thai people I just looked strange and unkempt. I cut it all off. When in Rome...
So, for your question #1: You don't have to have a visa when you enter Thailand (I assume you're US, UK, or AU). An agent can set it up for you to get a Non-O after you're here (at least they were able to in my case). ~ EDIT: I just remembered the recent news that the initial stay period for visa-exempt entry got reduced from 60 days to 30 days, so that could make this method trickier, but an agent could probably straighten it out.
Question #2: You can come on a one-way ticket, but the rule is that you need to have an onward ticket to show when you arrive in Thailand (some say you might even be asked to show that by airport staff while you're still in your home country, but I don't think that happens but very rarely). In reality, folks are almost never made by Thai Immigration to show that onward ticket (I wasn't, and other people I know weren't)—but you need to be prepared in case you're that 0.1% case who gets asked. Easiest thing to do would be to buy a cheap ticket to a nearby country that lets you do visa-exempt arrival like Cambodia (I mean before you fly to Thailand, so you'll have it on you as you're entering). It will be something like $60-$70. If you hate to waste the money, you could actually use the ticket, but then you'd have the extra expense of that trip, including a re-entry permit for getting back into Thailand.
Another rule is the one saying you need to be able to show 20,000 THB (or your home currency equivalent) upon entry. Again with this one, I've never heard of anyone being made to show this, but of course you want to have it on you just in case. And you probably would anyway, coming to Thailand with the intention of living here. They want to see it in cash, presumably because that's the only quick way they could verify it while you have 100 people standing in line behind you.
What's so scary about that? It only says that they'll be reviewing the visa-exempt entry scheme. If they remove that, at worst tourists would simply have to apply for visas before coming. That's not a huge problem.
John, I was/am in the same boat and was urged by multiple folks to go with this way:
<You come in on a visa exempt or tourist visa entry, get your funds in place then apply for the 90 day Non-O visa inside the country at the immigration office where you live, THEN after you get that you wait and apply for the yearly extension.>
That is my plan at this point. It sounds like it's the easiest. Plus I was a bit worried about the police clearance certificate thing because I have an expunged 27-year-old misdemeanor on my record, and no one could tell me whether the Thais would understand that it was an expunged charge or would just deny me because there was something there on my record. Thus, I will need to go with the Non-O applied for within Thailand because with that route they don't do the police clearance thing.
Believe me Tod, in this realm, every answer can easily lead to another question or five, and I think you know that. 😁 Okay, well "unlimited entry/exit" is more info on it than I had found, so I thank you for that. I was hoping that was the case. That was one main thing I wanted to know—whether by default it is limited to like only 3 entries a year, or means unlimited entries, or what. They don't spell out these details, which forces newbies to pick things apart and ask follow-up questions. For me it is a very important question because I'm not interested in any one-year arrangement that would lock me into staying in Thailand the whole year (again, this view presupposes a return to relative normalcy next year regarding international travel).