Ahh, well maybe it all depends on what value you place on availability and flying the aeroplane you want to fly.
I do know that if we sold the Cub today we would have had our flying for the cost of the fuel and insurance, as we have done the maintenance ourselves in the hangar of a friendly engineer, and the aircraft has actually been an appreciating asset that the tax authorities ignore.
So, cost price less resale value has covered the fabric, the annuals, and an engine rebuild.
Yes, we have spent time getting grubby and/or covered in nitrate and butyrate dope. We probably can't justify owning on a bean counters abacus. So what! The fun we have had nobody can take from us.
It's OK to spend money on your favourite toys. Regret what you have done if you must, it's better than sitting on your money and then regretting never having had fun.