Some of the things I am concerned about are the carpets (older, cheap carpet to begin with), windows (do not open and close well), painting (do all the walls need to be painted white?

I'm in Chicagoland and we have what I call a "seasonality effect." 

I am considering buying a quadplex as a house hack, but the eventual goal would be to move back into my current primary residence rather than buy another, so the seasoning period for me to get another loan would not apply.

It will be not only complex (but doable) to secure financing for it, but the real issue is that if you ever want to sell it, it will be super difficult for prospective buyers to secure financing unless they are seasoned investors which limits your potential buyer pool and potentially your offloading price.

I have a 3 BDR one bath  house in Maple Heights Ohio that I am considering renting to section 8 tenant .CMHA chart for the house zip code showing a max rent of around $2000 for 3 bedroom.I know market rent of my house is approximately 1300-1400 $I am adding efrigerator and oven.The house is older but in decent shape.

Typically DSCR programs have seasoning requirements from anywhere on average of 3-6 months, which means in order to use the newly appraised value, you would need to wait a little bit (although there are 0 months seasoning programs).

The "BiggerPockets Real Estate Podcast" is another resource I would suggest listening to for advice from seasoned investors.

However, your credit could also be impacted if you're co-signing or jointly applying for the loan.Regarding the funds, lenders usually require that the down payment funds be seasoned, meaning they need to be in the account for a certain period, often 2-3 months, to ensure they are not borrowed.

In the Bloomington-Indianapolis market, establishing these connections can provide you with off-market opportunities, mentoring, and invaluable advice from seasoned pros.

We also have a strict policy that anyone 18 or older living on the premises must be properly screened and approved.