What Are My Options for Extending My Stay in Thailand with a SETV?

I don't have any problems with it. Especially since you have a multi-year history of doing the same thing (i.e. leave depressing Oregon in November, return in March). I think you're a valid tourist.

doesn't really sound like all that bad of a plan. Enter on a tourist visa get 60 days, extend it for 30, fly out, come back on a 30 day visa exempt entry and a 30 day extension. That will take you to the time you need.

Should work fine. OR while you're in Lao pick up another single entry tourist visa (and then you won't have to get an extension).

it is possible as you have it planned. Make sure when re-entering Thailand for the 30-day exempt, to have a hotel booking for the first few days and an out of country ticket within the 30 days (sometimes an outward ticket within the 60 days is accepted as they know that you can extend the 30 day exempt for 30 more days) and have CASH minimum of 20,000 Baht or the equivalent in another currency ready to show. Preferably you should do the re-entry for the visa exempt by a land border, Laos to Nong Khai is known for leniency and easiness

There nothing to worry about you got your tourist visa just go they won’t stop u boarding with a setv and all the rest can be worked out along the way border runs visa runs etc it’s all part of the adventure have a good trip👍

Kathy, please can you confirm your passport nationality and previous travel history to Thailand

Nationality?