Paul vastly differ in quality and price.

I'm considering a similar scenario to what you describe, a relatively high quality SFR BRRRR that about breaks even on cash flow after considering all taxes and equity paydown, but not Capex reserves.I see what you mean about holding the asset and eventually owning it with no initial equity investment.

I can't speak for Chicago specifically and not a lawyer but in most juristrictions, the fence IS placed on the propety line and there IS joint responsibility for it.

Where should I go for more information before I speak to an architect. 

I would recommend listening to the following Podcasts (one on SFR and one on MFR):https://www.biggerpockets.com/renewsblog/2015/12/1...https://www.biggerpockets.com/renewsblog/2014/03/1...3) Personally, I can't really speak to this because I self-manage.

This is one of the lowest quality neighborhoods in the entire Cleveland area.

Like I said, I'm speaking from experience.Give yourself a 30 day cooling off period. 

Anyone in this space, i would love to learn what you know or atleast love to speak on this space with you as I know it’s best to speak with someone actively doing it.

I don’t mind paying for quality because I know this will help my business.Thank you for your time,“D”

I would urge you to speak to as many advisors as you can to see who is the best fit.