If you have to wait for funds from the sale it will be whenever that is.
If you have the means without the sale you can go whenever.
You can get a visa in advance or just fly in. Either way there are extension options in county.
I mean if you can afford it you could fly to Thailand this week. Not sure if you could get all the stuff for the dog that fast.
Now if you have specific questions about certain visa or extension options or the pet process I think it would be better to ask those.
But time? It will take as little or as much as you make it.
Your funds and if they are tied into the house and the dog are the only things that at all complicate it time wise. Other wise there is nothing stopping you from doing it as fast as you want.
The issue is and has always been that people (including you clearly) have been using these and similar visas as long term tourist visas.
No harm no foul IMO to use loopholes. But you have to be aware said loop holes can end.
Seems like a crack down is happening.
You have a few choices.
1. Get a visa that is more in line with what you want.
If you have the money Thai Elite is your best bet. But since you run an online business you could possible get a visa off of that as well.
2. Focus on the Nomad part of being a digital nomad.
Thailand normally seems to have no problem with people sending about half the year as a tourist in Thailand. So you could stay in Thailand 3-6 months and then travel in other countries for the other 6-9 months.
3. Go to a country that is more open to long term stays.
Some like PH without loop holes will allow it. PH specifically allows many nationalities to extend up to 36 months and then border bounce and start over with less than 24hrs outside the country. (Think dinner in Singapore) Others have loop holes you could use that like Thailand may go away. But in loads of places there are always loopholes. Thailand has long been one of those places and we all know it have heard of someone who has been in Thailand for decades without a true long term visa.
4. You could find another loop hole that is working long term for Thailand. Like I said Thailand has long been a country known for them.
Pre-covid IMO the writing was on the wall that they were going to start cracking down more. Post-covid we have seen people who used covid extensions struggle to get back in without spending significant time outside the country. And of course reports like this.
Thailand doesn’t seem to want long term tourists. It might have nothing to do with people like yourself but you are clearly caught up in it. Doesn’t really matter if they are targeting you or random Chinese nationals (as another comment suggests) with these enforcement changes. You have to deal with them.
I personally don’t think option 4 is a good option myself. But I’m not you so maybe you will.
Either way education visas seem to be out for your personally.
Utah County, Utah, USA is still doing online marriages if you need to get married and find the Thai system a challenge.
If one of you is American it is great but neither has to be. And it should be recognized in most countries since in paper it is just a marriage and they have no need to know it was online.
If she really plans to stay over 60 days she should get a Tourist Visa so we can extend to 90 days.
If she may stay less then 60 she can enter exempt and extend and do a border run if she wants to stay longer than 60 which could get her up to 120 with the extension then and 2 entries.
Hard to say which will be cheaper and easier.
Not sure if her current flex ticket will work if asked or not. May be worth buying an onward ticket if she can’t make it show leaving in less than 30 or 60 depending on how she enters. Google onward ticket for options that are cheaper.
at this point she might be fucked for life. At least for tourist visas. She’s likely flagged in the system for lying.
Really going to depend on the file notes and what the interviewer thinks. The notes will just create a bias for the interviewer which is going to make it harder.
But she better be super honest if she tries again.
I’ve heard of people who lied and tried again a few times with no luck. Never personally heard of anyone who lied and later got it but I am sure it has to happen. In general we hear more about the bad than the good.