I am currently a W2 employee.

If your current carrier inspects or if you try to change carriers, you may have issues. 

I've been sucked in lately, and been learning all I can; I'm 21 currently, with a goal to own 5 cash-flowing rentals by the time I'm 30.

Everything was original and needed updating to make it appealing to current buyers.

I currently bounce between Washington / Idaho / Hawaii / Arizona.

That is where I draw my take on Sell/Rent my biggest fear is the "What if Factor" - drop in tourism, association comes under litigation, hurricane (This season looks like it will be "Very" busy), Sickness or health issues or other.

It is a townhouse and the adjacent property (that previously had an identical interior layout and size) has gone through a renovation to expand the kitchen by approximately 100 sqft, and add a second bathroom.This adjacent property is currently renting for $300-400 more than what I believe I can rent my property for.

My goal is to start learning and hope to buy my second (we own our current home) property within the year to start my real estate investment journeyI got interested in Real Estate investing because I want to be able to have a large family and give them everything they need (college tuition, family trips, emergency fund) and want to grow a portfolio with constant cash flow to allow for these things. 

I'm planning a detached garage ADU conversion (tear down) and am currently upgrading my main electrical service/panel on the primary residence.

I put my 10% down, and am looking to insure the property while I deal with current owner residents.