I think they pull a record every time you apply for a quote which may affect their pricing tools.

Ive had a 5 year and very informal relationship with this landlord so no written records  were kept.  

Keep good records, minimize your debt, and try to clean up your finances before you apply.Most lenders are looking at the black and white numbers.

Financially, would it be smarter to purchase a rental home first (if we find one for the right price) or should we purchase our own home first then potentially rent that out when we are ready to move again?

I've recently had a perspective change due to listening to Rich Dad Poor Dad on audible, as well as some of Brandon's books, and im seeking to make a change in my financial, personal, and professional life.

Thanks @Kim Heretick and @Wayne Brooks The Counties I am looking at do not have their records on line. 

The purchase is said to be made subject to the underlying financing, hence the name.You can search for forum and blog posts on "subject-to" (or "subject to" or "sub2") using the BiggerPockets search icon (the "magnifying glass") at the top right of every page.For the record, the exact mechanics of Sub2 vary from state to state.

My goal is to get my financial freedom and get 5k a month in passive income as one of my initial goals for real estate. 

All said I recommend that you do it, if you don't come out as great as you thought financially, you will come out a wiser man!

Now this company went one step further and recorded owner carry contracts to the end buyer  so more of a wrap program.. well those buyers started to default.. and since this team had the wrap they needed to pay the underlying and well it was a house of cards.. once they had 10 to 15% vacancy or non pay they could no longer debt service the underlying and now the original owners were getting notices of default.. and then they start filing complaints at the AD.. and well it becomes a scheme to the state..