If location is strong and not much vacancy in the market do not expect landlord to negotiate much at all and for them to be very strict on what they will agree to.

If that makes you or your wife uncomfortable, you could consider a property manager who would be the contact for the tenant and require all property communication to go through them.You need to be well-informed regarding laws in your area. 

Trying to further my knowledge about the Illinois market and landlord laws.

My advice to my daughter and son-in-law as they did not want multi-family, either, and wanted to buy a home to live in,  not just investment property, was to buy something that needs some work, plan to fix it up within the 2-year tax-credit time period, sell and keep profits tax-free, then buy another one that needs work and repeat until children need a solid school district.   

A 10% cash on cash ROI could be slashed with a single percentage increase in interest rate.Secondly any mortgage laws, requirements, etc. that may change or negatively affect your property can be mitigated.

Each state has different contract laws so you have to use one that is legal in your state. 

People are starting to get creative - if you are familiar with STR laws in your area & if that area is a destination spot, using that to your advantage might be something you are looking in to. 

You can usually comp properties out yourself, but you need to know if there are any major structural problems. 2) I would consult a local attorney to ensure you are considering all applicable laws (usury, registrations etc.)3) This is up to you.

VA loans are strictly for owner occupants. 

Find a local law firm quickly and pay as much as you need to for their valuable guidance and representation.All I can say to make you feel better as you, yes, bite the bullet and forget about more leeway, is tell you that I've made the same and bigger mistakes that you have in the past, and I've come through.