Your history is quite typical, you shouldn't have any problems but then again nobody knows, have the three proofs ready, an onward ticket, booked accommodation, 20k baht.
No worries, wherever you are staying will file a TM30, once you get to your home you get your landlord/self to file. The most recent always supercedes the previous. Your first 90 day report will always be in person at your local immigration office, you have 14 days before and up to 7 days after the due date to appear in person. Subsequent filings can be done online if you stay 90 consecutive days. You can file online between 14 and 7 days before the due date. From 6 days before till 7 days after you must go in person.
Typically you need to provide proof of ongoing care, diagnosis, treatment plan, at a recognized medical facility with appointments set up for the next 6 months at least.