You could get the 90 day non O, enter Thailand then get a re-entry permit, leave for your work rotation, return and apply for 1 year extension and when you get the extension, get a multiple re-entry permit then you're free to come and go as you please. There may be a bit of dates juggling while under consideration but it should work out about right if you are on a
To avoid any ambiguity, just get your home registered online and take 5mins to update your TM30 any time you come back from overseas or domestic trips where a hotel would probably registered you.
By the rules, yes, but if you are not filed in Bangkok then don't worry about it but if you stay at a hotel and they file, then you will need to refile back in Pattaya because your Pattaya address will no longer be valid because of the hotel filing.
As mentioned, it's up to the IO at the airport but as you have been away for 5 months, it's fairly clear that you are not trying to live here on visa exempt and extension stamps so you should be ok provided you have the 3 requirements when you arrive, if asked for them.
... you cannot get a re-entry permit on a visa exempt stamp. Once you stamp out that exempt stamp is void regardless of the days remaining on the stamp.
Yes almost certainly because your hotel TM30 will be logged with immigration and won't match your rental place when you go to do an extension or even a 90 day report.