What saved us was a financial report showing we were way low on percent of units that paid their maintenance dues. 

Or, can we keep it on our current home (i.e. our investment property) for the tax savings? 

We are looking to start March 2019 as we will have 50k saved up to start.We have have solid jobs in Chicago and are looking at Milwaukee to get the ball rolling,.

I'm not sure what your financing strategy is for your early phases, but it will save you time and money in the long run if you're familiar with all your options now.

He does not have any capitol saved or home equity and would need some income while he does the work which would come out of my budget.

Was it saved from the rentals you already own?

You would instantly save on taxes by moving to another state.

Be sure to save your funds from arbitraging and buy property when your market is a buyer's market.

I put $25,000 into repairs, but could have saved $5,000 if I had gone with the GC's people instead of my own (at the time I had not quite settled on the GC). 

You say you can afford the mortgage even if the other unit is vacant but that you don't have extra cash for the other expenses of being a landlord.So...instead of buying a single-family home instead, can you buy the duplex, keep up with the mortgage, sit on the other unit for a while until you've saved up some cash, then rent it out?