Other than the 1 property I am renting my family's taxes are pretty straight forward with a couple W-2 and no LLC, so when I got the $1,700+ quote for tax preparation it seemed a bit much.

It should be relatively straightforward to begin discussing the goal-setting and planning process necessary to begin transitioning from current state to future state. 

Hey James: These are note from an attorney that we use to evictions hope they help you.If you need exact notices may be I can paste them on here so they will help everyone is IL that needs to do an eviction.Eviction in Illinois Are Done By The Following Rules:There are some exception like the city of Chicago, Evanston & Cook County but the rest of the State Of IL is fairly straight forward.

Very tech-forward and straightforward experience. 

Thank You for the input, it's confirmed there is not a straight forward traditional mortgage option.I'm looking for a property in the 100k range.

I was thinking of starting a rent increase for my 1 bedroom tenant voucher due it being low and well under fair market value(Based on  hud and zip code) but my tenant is in the process of having a caretaker for her disability and getting approved for a two bedroom voucher.

What rentals are not subject to fair housing law?

Quote from @Cari Sweet:  This sounds like a case for Fair Housing- Familial Status discrimination. 

From a tax standpoint, there are additional disclosures to make when selling a business asset for less than fair market value to a related third party. 

That's pretty fair.