The "ridiculousness" of the 5 year visa would be taken care of from the top, not by some pencil pusher. That said, Thai consulate employees are notoriously grumpy everywhere.
That should be ok. When performing your border bounce, make sure to have all the required documents: ongoing flight (or bus or train), 20k thb in cash and a hotel booking a few days. This is when they are more likely to check these.
There's no actual set limit, BUT, you will be questioned by immigration after a few back to back entries, and eventually refused entry, as they will want you to get a proper visa.
Why don't you simply get a job for 3 years and learn Thai? That's the simplest way. You make it seem like you're unemployable in Thailand. You can communicate in English? Just teach English.