Anyway there are so many more reasons to investing than just straight cash flow (though IMO you should never buy a property that doesn't at least break even after all of your costs).

I was curious if any multi-property land lords have a good system (or suggested products) for keeping expenses straight and annotated throughout the year for their different properties.I have separate LLCs and bank accounts for each property, however when I go to export and classify most of my expenses for the year, I'm finding that I forget what some unlabeled (or hard to decipher) expenses were, and thus may be classifying them wrong.I'm looking for something like Quickbooks, but that can handle multiple LLCs/Bank accounts, because as I understand Quickbooks requires different user names for different businesses.Note: I have tried Stessa (and honestly, what it does is what I'm looking for....) but because I use smaller regional banks, the connects to the accounts have troubles several times a month, and I end up having to go back and manually import transactions anyway, so it ends up taking more time than it saves me.Thanks!

@Kevin HerronTo learn more about real estate investing in Chicagoland, you should definitely check out the Straight Up Chicago Investor podcast, which @Mark Ainley and @Tom Shallcross host.

Would it make more sense to finish this Property and get secured before I grow my portfolio, or jump straight into acquiring more properties.

As mentioned the SDA by Michael Blank is pretty straight forward or the model by Corey Peterson is also an easy starting model to use.

Very straight forward, honest people.  

If I were to go the route of REI without a college education straight out of high school... what are the prospects of that?

It seems pretty straight forward, but since this is my first cash-out refi, am I missing anything here? 

They are what they are and what the tenant is paying for.You need to draw a no compromise line in the sand and teach tenants from day one or you will end up being owned by them.When they ask for something either give a straight NO or tell them they will pay for it.

He's showed that he can pay on time for 3 years straight so I think he deserves the benefit of the doubt.