@Jake Islas  pretty basic when it comes to investing the 4 door rule and the 5 door rule don't say that to any agent you run across they will know your a little green.1 to 4 banks look at as resi type loans... 5 doors or more are commercial.. generally speaking unless your a very high w 2 wage earner or very cashed up 1099 earner more than 4 resi loans is tough.once you pop into 5 doors or more and commercial the financing becomes completely different.All agents that do commercial real estate are investor friendly that's all they do.. so you don't need to specify that again showing your experience level is important if you want the best agents working with you.. if the commercial agents even get a wiff of a newbie your not going to be dealing with the best ones.

We are dealing with a lower class community where high school is the absolute highest level of education and there is little to no population growth.  

800k is a lot of cash doing nothing - - but money market CDs aren't worth the effort (at this time) either.I would guess your 7 units are SFRs, so you should be able to get some level of LTV in a cash-out refi and use that to fund another purchase.Caution: don't try this on all units at the same time!  

Ideally the PM I work with will be resourceful, honest and has a certain level of business acumen.

The investor purchased the asset with the intention of renovating the units and adding value by increasing rents.South Shore remains to be one of the most undervalued neighborhoods in the City of Chicago relative to employment, average house hold income, occupancy levels and rents.

I suggest putting in at least 4 inches to cap your building and improve energy consumption, At the time of the tear off coordinate renting a blown insulation machine too and you can add insulation from the roof into the attic/crawl space above the ceiling level to avoid interior repairs.

Your scenario comes with a few loan level pricing adjustments.

Ideally the PM I work with will be resourceful, honest and has a certain level of business acumen.

Many posters on here are giving opinions based on various experience levels and particular strategies they have found success with and see value in.Someone making 300k a year isn't living off of the investment cash flow.

Final and most important point, surround youself with people who are very knowledgeable and look at for your interest becasuse I have found in life that most things can be accomplished if creative thinking is done but most important planning ahead and that might, depending on your level of expertise, mean you need to find a few investors or CPAs, or investor groups to hook up with.I am investor and every true investor I have met, actually loves helping people succeed.