This is located in oak harbor WA on Whidbey Island if that is pertinent for calculating a deduction just a general idea would give me a huge help at least would be a starting point the rent is higher than a lot of similar apartments however as I stated it's on property but the lack of kitchen almost cancels out the benefit of the setting.

A homestead usually helps with lowering taxable value, but it's kind of screwing me over in this situation.

Selling for $1M with a $100k mortgage is not taxable, if you paid $1M for it.

Be familiar with calculating ROI, prospective cash flow, and other important measures.

However, I think from a financial perspective, it's likely a better idea to pay off the debt or add the money either to a taxable brokerage account or a retirement vehicle like an IRA.

Also, in our experience, 95+% of agents have no clue how to calculate ROI, Cash-on-Cash, Cap Rate, etc., so what are they really going to help an investor with?

Yes, as a home owner you are on the hook for any other miscellaneous expenses that arise but that's why you take out reserves every month in your calculation. 

That’s a complicated set of questions but it insures you get past every reason it would be taxable.

Retirement distributions are considered taxable income(Federal and state).You mentioned self-managing the rental properties so it may be that the income will offset against the rental loss.However, you will still be subject to the 10% penalty.Have a conversation with your CPA and ask them to draw you up a draft of several different situations and see if that is something you want to move forward with.

Just make sure to consider PMI (private mortgage insurance) in your calculations since you'll be putting down less than 20%.