I own it for 6yrs now but I can't seem to reach the second home.

My goal is to reach financial freedom young so that I can enjoy this life to the fullest, and give my loved ones everything they have missed out on.

You can easily tag each transaction using categories that synch to your Schedule E for tax time.

Stable, conservative & easily accessible during the interim.If you put in a Roth IRA, it becomes a lot harder to tap into..

Small delays in repairs, cleaning, or scheduling contractors can easily turn a simple turnover into weeks of lost income.

It's not a matter of luck but having an understanding of the local laws, neighborhoods, and connecting with the right people (building your team) to leverage their expertise.Since you currently live in Illinois, and unless you work remotely & can easily relocate, it's probably best to keep searching for a decent property to house hack to take advantage of owner occupant financing.

This would give you access to long term fixed rate debt financing options, make it easier to self manage and allow you to more easily sell if you find real estate investing is not for you.Secondly, a positive cash flow of $24K annually from 18 units seems like a very low return given the prices larger multifamily properties (10+ units) are currently trading for in Snohomish County. 

And honestly, anything that lets them stay longer and safely is usually worth it.If you say no, they’ll eventually reach a point where they physically can’t use the bathroom and will have to move — and then you’re looking at a full turnover after 40 years, which is rarely cheap.If it were me, I’d allow it with a signed addendum that fully protects you, and require licensed professionals only.

When I'm buying I can easily drop a realtor without a negative impact, but it's tougher when you're selling especially in a tenant occupied property.I want to sell my property without a realtor.

Both units have been fully updated, each could easily rent for $1,200–$1,500 per month, and the annual taxes are under $3,500.