Even with this prices, some triple deckers in the areas you mentioned still positively cash flow while smaller single condos may run at at a loss, depending on the terms.

Single.

There should be nothing barring you from locking the water spouts.

I use to stay up until 2am every single day to do BS tasks, just to keep the deals coming.

If you are starting out I would suggest getting a single family home first.

Does anyone have experience with converting to a multi family property during rehab of a single family? 

Nope it's just every single person lowballing the price.

A single tenant - even in an apartment - can cost you thousands of dollars in losses before you can say, "I don't know what I'm doing!"

I invest in single families in the Milwaukee market.

We are working hard and doing well in the single family flip market but im trying to develp a plan i can put into motion for larger multifamily in the next 6 months while we continue to do flips on single family to build capital.