Yet, one of us gets the advantage of living there, but I can't think that would be for free.

I seem to be able to turn any conversation into real estate, even with friends (which has opened the doors to opportunities), but that certainly got me rolled eyes with my wife.I knew talking advantage of deals would be an issue because she wasn't TOTALLY on board, and by the time I ran numbers passed her there would already be 3 offers on the house I liked.

The home inspections is why I want to get into this in the first place, because I see that advantage I have as well and i am on the inside of my market everyday.

One huge advantage to this is that it will clean up Zillow postings that are overdue/expired or already rented out.

I am unsure if I should pouring my money into the stock market to take advantage of compound interest at my young age, or save this money for a down payment on a rental property.

Since I no longer have a day job, I just see it as a replacement as I wanted to be self-employed and I take advantage of being able to take my own deductions. 

Why would I continue to save in my 401K and why would I not take advantage of this "10% discount" now and pull $100,000 out of my Retirement and invest in good quality rental properties. 

The idea is to repeat the process.If you bought one property a year for 10 years your cash flow is $36,000 a year plus all the advantages of depreciation, property tax deduction, mortgage pay down and interest deduction.  

This can be very tax advantageous for the seller because to the extent you can engineer this, she could possibly pay zero tax on this if she can keep her total income for each year under her deduction amount. 

But there are still some great advantages to owning your primary, such as: Your mortgage interest is tax deductible, and there is $500k capital gains tax exemption for married couples.