What should I do for my Thai visa situation with multiple entries and borders?

Hi! I have a quick question:

What should I be doing?

This year:

1. VE+Extension (60 days). After 60 days left the country for 10 days.

2. Flew back in - VE (30 days). Then left the country for a week.

3. Flew back in - VE + Extension(current) (60 days).

Vientiane will be my first Thai SETV. I'm a US passport holder. No overstays. No prior SETV/METV or land crossings.

Was in Thailand for 36 days in 2018. 30 days visa exempt plus 30 day extension(of which I only used 6 days). Didn’t want to risk an overstay.

Planning to fly to Vientiane then land crossing then fly back from Udon Thani. What are my chances?

Also - What I've noticed is when flying in Business Class - IO is easier - or have I just been lucky?