I do JVs like this all the time (Just completed my 5th).Send me a DM and I can provide some details (little easier than by msg)

For me, probably.If you're toward the $325K price, I think this decision becomes MUCH easier for me.I'm curious what is causing you to hesitate with waiting?

Harder to find a motivated seller willing to sell at a discount or creatively than to find any old seller and easier to find any buyer than one that can buy at a big discount for cash or with creative terms. 

It's easier to keep track and ensure you don't spend it.

You can't hit the target unless you pull the trigger.

It'll be 'easier' to get a loan as individuals rather than an LLC (specially if it's newly formed).

My target market is Wilmington, Delaware which is another shrinking marking and I would argue doesn't have the same economic prospects that Milwaukee has.

do you think it mite be easier building a small granny in law suite with a desperate entrance?

That’s really about it.Go visit the target market, study it and make a decision as what to buy

I've been "driving for dollars" here which is good but I'm also open to starting with a list of homes and targeting that way.