There are property management companies, but looks like I have to sign up for a full service to do the annual inspection.

Long-term goals could involve building a diverse portfolio, achieving financial independence, or even transitioning into real estate full-time.Ultimately, the journey in real estate investing is both challenging and rewarding.

But I would definitely get your loan officer to contact the seller's agent to go over the loan process with them.

You could have a duct cleaning service clean them.

Consulting with a local real estate agent who specializes in vacation homes can provide valuable insights and help navigate the intricacies of the Seattle market.

Setting up automatic payments for recurring expenses or using online bill pay services can help ensure that bills are paid on time and reduce the risk of missing payments.Overall, the key is to establish a consistent process for tracking and managing expenses for each property/entity to effectively manage your funds and ensure that expenses are properly allocated.

I was able to get comps from a friend of mine who’s a real estate agent, but how do I go about finding exactly how much work needs to be done to the home in terms of a dollar amount?

First year and beyond is typical on a schedule E, same as a LTR unless your providing substantial services.

Does anyone have any recommendations for professional services in this area? 

I stick to sponsors who have at least one full real estate cycle of experience with little to no money loss...ever, conservative leverage, high skin in the game, reasonable compensation ( so they aren't incentivized to push the risk envelope) etc.