How many times did you leave Thailand, and how long did you stay out each time? And were you actually travelling around Thailand? They may deem you don't need a Multi entry, and just give you a tourist visa.
They may also determine you are trying to live in Thailand, and suggest you apply for an appropriate visa.
In all legality, you have to show onward travel within your initial exempt or visa period in Thailand. Book a flight to Kuala Lumpur for the end of the initial visa period. Heck go hang out for a few days there. This will serve the purpose to get you into Thailand.
is right, a multi entry visa is your best bet. But that would also suggest to immigration that you need the multiple entries.
Also, you would definitely need a departing flight in order to get the visa.
You could also come in on the single entry tourist visa, extend, and then go travel to a different country, then return visa exempt. Your life would be easier if you are moving around Thailand, not staying at 1 address though.
But bottom line, whichever tourist visa you use, you will need to leave Thailand several times.
Are you incapacitated in any way? Most of that stuff is very easy to do on your own.
But anyway...
You may need to go to several different sources for most of that. There is food EVERYWHERE in Thailand, so there is no need to cook or be cooked for. And there is delivery everywhere.
As far as getting a phone, just go to the mall, buy a phone of your choice, and they will set the SIM and everything up for you. There are pharmacies everywhere too. Not sure why you would need to be set up for that. As for Doctors, just go to one of the hospitals (Like Bangkok Hospital) and register.
You say you are lazy. This is something I do not understand.
Define "too ill to travel". When I hopped in on a walker with my broken leg in Bangkok, the immigration officer told me and my gf, that if I was in any way mobile after my extension runs out, I should leave and re enter. You basically need to be stuck in a hospital bed or unconscious for a medical extension to be given. As a side note, wheelchairs are the BEST way to get through SE Asian airports. 😁