Before covid I was doing back-to-back tourist visas. Never once did I get denied entry. It is a risk and I always had a plan B. This is post covid times so who knows.
I am 47.5 I too am waiting for retirement visa.
Once I got stopped by an immigration officer. They asked me some questions, yelled at me for a few minutes then sent me on my way. The whole time I was very polite, very respectful "yes sir, no sir". I can easily see how a person might get an attitude with the IMO, which would lead to being denied entry. - Don't get an attitude.
The IMO told me that if I am going to do visa runs I should spend a couple of weeks outside of the Thailand each run, so I was doing that. Australia offers MTV's to Americans probably everybody else too (Pre Covid),
That's my advice and what has worked for me.
A) Travel by land when possible (better plan b options)
B) Stay outside of Thailand 2 or 3 weeks each run
C) If/When the IMO supervisor yells at you, remain friendly, respectful, let them know you know you are guest and you love their country.
I recommend doing that sooner than later. Some people get approved in hours, other people it had taken weeks. I was approved in 3 weeks.
I recommend you ask for a hotel recommendation within this group. A hotel people have had good experiences with. I think part of the slow turn around with the Thail Pass is that hotel didn't know what they are doing.