Typically lenders do not allow this but if they do you would ahve to go through a full underwriting to confirm you qualify to make the payments.

Is that typical for insurance placements in that market or is this the high end you would expect for this property? 

W what typically went wrong in your case? 

Like almost everything else in life: Short-term pain for long-term gain!

It was a typical house purchase deal.

Since you're currently using the property as your primary residence, the cost of improvements made before it's placed into service as a rental wouldn’t typically be immediately deductible.

Investors can always benefit from working with someone who knows how to align opportunities with specific strategies.Are there particular types of properties or investment strategies you’ve seen gaining traction in the Seattle area lately?

Living in the property for two years likely allowed you to claim the capital gains exclusion... up to $250K for singles or $500K if married.

Yes typically you'll file the wholesale activity on a schedule C unless it was done in an entity (S Corp, Partnership, C Corp) but I see above you don't have these.

It's low risk and tax free on the gain.