I am currently contemplating whether I should get my realtor's license in Washington state.

I am contemplating on taking the risks and buy a few of these and hold and rent for years.

For example, we once were contemplating moving to an LLC but the transfer tax was 4.5% of the market value of the property.

I'm contemplating the area of short-term rentals (thru Airbnb for example), as well as house flipping.

Getting to here has been a 2 year journey - reading, analyzing, contemplating, no action, repeat.  

Am I going to learn or re-learn truly useful stuff, like the above for how to help mothers with newborns get a right-sized house for the expanding family (which incidentally might benefit Quinton the REI in a bad HML), or is it going to be a bunch of useless mind-numbing junk that makes me want to contemplate self-harm?

We are contemplating on finding an agent or selling ourself as we speak..

Especially if you're contemplating taking on a large debt level for a car wash, real estate, etc.  

We are contemplating building spec houses for resale, rental houses, or a trailer park.

I am holding onto it until a developer contacts me, but I have been contemplating if I should build a house and sale it.