@Matthew OlszakThanks for the straight forward advice.

Seller financing puts more risk on the seller so this is a key factor to the deal.Don't dive straight into prices and how bad you want to buy it but try to find points to convince him to sell.

I recently completed my first house hack and am now moving forward with searching for and purchasing a SFH or Duplex that will be a straight rental.

Point is, seriously pull out the charts for the median home values over timeline, a reasonable time in market years say 30+ years and it will blow your mind how small those changes actually were, and how much the market keeps snapping right to the steady straight upward trend. 

@Carlos Ptriawan Agree with your comments, I haven't seen any MFR with workable numbers in markets I like or I'd have gone straight to that.

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.