I'm a little out of the real estate learning and trying to get back into again.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I will be attending a real estate meet up tomorrow night in Seattle but would appreciate any advice before the meet up. 

It was honestly luck, I didn't know much about real estate I just knew I needed a house that was unappealing to others to be able to buy it and have it fit in our budget.

With your background in real estate (STRs and assisted living), commercial MAY make more sense and then if there are any residential deals you can take them as well.

Squatters are a real problem nationally and a study found that they target not only vacant properties but those advertised for rent or sale that offer 'immediate occupancy.' 

Basically wanting to pay two years of Real Estate taxes in 2025 and deduct on 2025 Return when filed in 2026.

With the two lots together they could be sold for 50-75k.. im doing research all day everyday to learn more and more about real estate investing.. so much that im nearly on the verge of divorce.

Real crap! 

If your comps were sold by a real estate agent and you are using them to justify your price, that is like trying to sell your car at a car salesman's price instead of an owner's price.In any case, if you need to lower the price, make sure that the price drop is a decent amount versus a "drop in the bucket."