Having a w2 job will do a lot for you in terms of financing a property. 

It pays to be well-informed about what is allowed in terms of rentals and how much you can borrow before making any big decisions.

What would you say bring the most in terms of property types?  

I get pretty detailed when analyzing comps, so I def need it to be nuanced in terms of linking to appraiser where I can find zoning, searching by subdivision or as to distance from subject property.

I don't think things work the way you imagine with the structure you describe, both in terms of asset protection, taxes, DOS and transfer taxes.The LLC structure is unlikely to give you any tax advantage - consult with a CPA before putting something crazy in place.For asset protection, you should have one entity (or more) just holding assets, separate from another entity doing the property management (public facing) - watch podcast 109 and talk with @Scott Smith.Here is a diagram to help you a bit in this question:

I'm planning on using my free time during the house hack to upgrade as much of the property as is feasible and has good ROI (in terms of either rent and/or equity increase or educational return) but am trying to find a good set of educational resources for DIY home repair.

In terms of apartment syndications, we are not trying to keep our money tied up long-term so that when we are ready to pursue our next rental, we can have the funds within a reasonable amount of time.

compare the two in terms of total payments.If you have lots of equity and not much steady(W2) income, HELOC may work better.

The Areas that stood out to me (primarily because they at least at SOME level of growth and were lower than the Chicago average for violent crime) are:-60638Clearing neighborhood-60652Ashburn neighborhood, Scottsdale neighborhood, West Lawn neighborhood-60646Forest Glen neighborhood, Jefferson Park neighborhood, North Park neighborhood, Norwood Park neighborhood, Sauganash neighborhood-60706Norridge, Harwood Heights-60655Beverly neighborhood, Morgan Park neighborhood, Mount Greenwood neighborhood-60634Belmont Cragin neighborhood, Cragin (Belmont Cragin) neighborhood, Dunning neighborhood, Montclare neighborhood, O'Hare neighborhood, Portage Park neighborhood-60707Belmont Cragin neighborhood, Conti Circle (Conti) neighborhood, Cragin (Belmont Cragin) neighborhood, Galewood neighborhood, Montclare neighborhood-60803Howes Landing Boat Launch neighborhood, Laramie Square neighborhood, Navajo Hills neighborhoodNow I have no idea where these fall in terms of price or cap rates, but they are all neighborhoods that had decent to good growth and were (again) lower than the Chicago average for violent crime (still all over the national average) AND they are all neighbors I haven't heard much about around real estate circles. 8.

They provide nothing in terms of content - all they are is an information aggregation website with strong SEO.People don't realize how expensive these lame websites are for an agent.