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? 

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

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

Whatever you decide will be best for you - BUT - if you do re-finish the floors....MAKE SURE you do the prep & clean work....after sanding - sweep at least twice.....then tack cloth (you can make them yourself - basically a rag with mineral spirits - VERY easy) - I went over the entire floor twice - I might even suggest three times....it gets the "crap" out of the pores of the wood & lets the wood take the stain much better....and the more coats of poly, the better - but take your time - as they ALL have to dry...MAKE SURE they are dry...

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

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.

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?