I’ve had just about the same experience with thumbtack as you have, although I’ve not been using it as long and haven’t put in very much money. Most people that I’ve talked to put in ~$30 and stopped using it after a year without any successes. The stories I’ve heard about people who were really successful on the app went out of their way to make exceptional profiles and made great templates, but all of these accounts are secondhand. I wonder if Thumbtack is aware of how many people have had this experience because recently I noticed a spate of “free” quotes coming in.
In any case, it’s nice to read your writing! See you around the city sometime!