Make sure you have an agent, property manager, and general contractor on your team that are very familiar with the area.Most of those neighborhoods are block by block.Where are you from? 

Can you convert a metes and bounds to a lot and block?

~Unlist the old listing from the previous owner and create your own, blocking out the booked dates.

Tenant also agrees to the following:-All drains, waste pipes, and plumbing are accepted as clear by Tenant at the time of occupancy, and any material blocking them after occupancy shall be repaired at Landlord’s cost, unless determined by repair person that such blockage occurred during the time Tenant controlled the Premises and due to some fault or negligence of Tenant, specifically excluding blockages caused by roots or backups from the street.

PermaSeal recommended a drain tile system which I agreed to.

But Milwaukee is really block by block in some parts, you drive 5 minutes and it looks and feels way different.

My email is in my signature block. 

You'll probably only go negative in the months you block off time for your own use. 

It's cheap, it's near where we live, it needs to be rehabbed, it's the worst house on the block with a ton of potential.

If they were identical and one wanted a parking block painted and the other didn't care, who is to say the seller has to take the one that wanted the work done at any cost?