Start small, be patient, and stay connected with local meetups and online investor communities for support. 

Once you know you are ready to buy your first REI you need stay glued to sites like Zillow, Realtor, Redfin, and other FSBO sites to help your agent find a property. 

Stay hyper local.As for investing in Illinois: Get your head examined.

Get their advice and knowledge and maybe they can be a mentor for you.

My main goal is to build good fundamental knowledge so any and all help is appreciated!

Regarding S8, the leases are 1yr only, but S8 tenants tend to stay longer vs cash paying tenants.

I am active duty military and plan to use the property for deployments/holidays for my family to stay near relatives until I separate in 4 years, then to use that property as one of several future investment properties.

Airbnb with a minimum of 1 month stay could be a good reference too. 

This will be the largest bond sale in US history coming up which on top of the debt we are also running as well - if we have so much debt to sell I do not see rates going down, I think they may rise (or stay around where they are at). 

Here are additional comments:1) Buying out of state removes any local knowledge you have from assisting in your success, including knowing areas, people and costs. - We always recommend buying your first rental locally if possible and DIY managing to learn as much as possible before investing OOS.2) Lots of crooks and incompetents in the PMC world:( They both cost you money.- As already stated, you'll have a small portfolio.