Michael you can actually go the same day you arrive on a visa exemption stamp that is if you land within the hours of the immigration office....if you get a 60 day SETV you have to wait 15 days or at the 45 day mark however you look at it before you can get the extension at immigration...it’s easy and costs ฿1,900 for the extension
You can go Monday and get it done, no reason waiting until the last day to get the extension...pro tip CW closes Noon-1300 every workday so if you get there after 8am the chances of you being there until 1400-1600 or longer is highly possible...
2 land border crossings per year... in theory unlimited visa exemptions via air crossings, however the consensus theory is the I/O’s will frown on it after 3-5 Out/In’s in a row...get an SETV or if you qualify a 6 month METV
im going to have to disagree with you on the point of a private corporation dicatatin where i have to travel to. that turns into a Trafficking in Persons [TIPS] violation with lawsuits. any corporation can only advise and assist but can not Dictate where a person goes against their Free will...
the most likely stamp they will put in the passport this does indeed happen is the "Did not have enough funds [20,000THB]" which does not interfere with your entrance from another location...
Most likely they will not put a denied entrance stamp in your passport they will just detain you then make you fly out...at that time purchase a ticket to a neighboring country then take a land entrance into Thailand....FYI if your passport is on the approved list you can get the 6 month METV in Perth Australia
You should not have a problem entering Thailand with that history...however it is up to the Immigration Officer you go through at immigration to grant or deny you entrance....but I would not worry about it at all