My first thought is that if I can generate a design for 6 houses and shared community green space(rather than individual yards).

Wouldn't a landlord be subject to rent control based on the number of units on the individual property? 

Now again, of course, if they are doing "extra" things in the monthly management that you find you want to be rewarding of then you accept their terms of that %.

Does it simplify tax filing instead of having to account for all the separate individual transactions?

Online contracts will NOT fully protect your individual interests.

Rob Grove you can contact the owner prior to the foreclosure auction or go to the auction and bid.Most large banks won't deal directly with individuals once they foreclose on it, until they list it with an agent or online website.

@Paul GiloThe reward is not so much the few grand a year in economic benefit early on that I described with my "number crunching" but the fact that you are getting into multi-family with so little cash out-of-pocket as described in the last paragraph of my post.

if you have all your cash (eggs) in one basket you are taking on a massive amount of risk (and reward).  

They will likely send an inspector to show compliance with city code depending on the type of store fronts (e.g. a restaurant setup will have different requirements in many cases than an art studio, for example).I would certainly invest in getting individually city metered utilities so that the tenants pay their own utility bills and there is not some messy shared arrangement that you have to deal with.  

Be persistent and stoic in your pursuits and you will be rewarded greatly!