As others say there is no rule, but usually you won't run into problems as long as you are not "misusing" the visa system by being creative. As you can easily get a multiple tourist visa valid for 6 months and 60 days per entry, I would not worry too much until you reach this level of tourism. But no guarantee.
You can try to go to Immigration and ask for the application forms and the list of requirements. This will give you a pretty good idea about how complicated it is.
, there is no doubt that what the Immigration Bureau would like you to do is to get a Non-O single entry at an Embassy or zero entry at the Immigration and then have an extension to this Non-O. However, you are not gonna get at least not the extension (legally) without complying with the financial requirements, and the paperwork for the extension is comprehensive and somehow cumbersome (especially when you are new to it).
, you will get different experiences from different people on the border bouncing on a Non-O multiple. I know for sure that Poi Pet Cambodian border is not a station you should use for it. But if you stay one night outside Thailand and arrive by air I guess most experiences will be positive. However, the substantial requirements for getting the Non-O multiple at most embassies are the same as getting an extension at Immigration, but the paperwork is more comprehensive at Immigration.
As long as the previous visa has expired (multiple Non-O) or been USED, then you can get a new Non-O endlessly as long as you comply with the (current) requirements. I have personally held more than 10 multiple Non-O visas based on marriage. However, I will not recommend multiple Non-O visas any longer as some border stations do not like you bouncing out and in again every 90 days.
, yes, I was actually just looking at this. You might be able to get one ordinary 5-year Elite Visa and then a 5-year family member Elite Visa. Don t quote me for it, but it looks to me like this will add up to a total of 900k THB (600k + 300k). Try study the thailand-elite.com