At the same time you could offer to release them from their lease if they choose.

An "Authorization to Release Information" form should be secured - especially if the homeowner mentions there are seconds taken out on the property.  

Bring in residents and you bring in businesses that will cater in the evening, and hopefully this will extend outwards.

I would definitely do the studio apartment so it could be a student rental,  extended family suite or an art studio/man cave.

Keep in mind that the upon removal of the floor covering(s), the damage visible to the sub-flooring is likely to extend underneath the tub.  

I know some guys who market and rent ONLY to fellow military members for extended short-term housing and are killing it.

If at all possible, I would absolutely open all three of the second floor windows, it creates a nice balance and provides interior light.What the building lacks is a residential, attractive and welcoming entry, which will completely transform it without spending a fortune.A few questions... does the front property line extend to where the grass strip ends at the alley?

I have an extended cab F-150 that I keep stocked with tools.

If you are serious I would write a check when you agree on terms and either have a simple buy sale agreement ready with fill in the blank price, or pull out a tablet of paper and put the terms down and sign it.

Good development contracts design out municipality risk and have extended closings so you may be waiting a while for a commission or a sale of a contract.