We liked the selling agent, so we retained him, and found opportunity after opportunity was followed slowly.

Anyways, I'm starting to second guess myself about retaining the tenant that the previous owner had in one side of the duplex.

Landlords out there probably don't realize that this is not acceptable as the photographer probably retained ownership of the images while licensing them to the agent who sold the place to you. 

He too has failed to pay taxes in a timely manner and still retained his lot.

As it takes more time and money to replace a tenant than to retain one, be careful on just how much you change the rent, unless a specific tenant has a history of being a PITA.

One of these was offered to us essentially for free, but it would take half-a-million to update the property(energy efficiency, modern electrical and plumbing, etc) yet retain its 1880s majesty ... we would need to cut it into three ~1600 sq ft units (one per floor), but would need to be able to sell them for ~300K to make the project worth while ... the market just isn't there at this time.

You will receive an Addict award along with a habit; as well as learning and retaining useful real estate information without struggling.Brandon Turner mentions we are considered to be the average of the 5 people we spend the most time with.

Since this is a 600 amp service with SIX strands of 350mc wire the size of your thumb we had to retain the services of an engineer to draft plans along with my electrician and I figuring out how we would replace service with an occupied building.

From my understanding of the Indy market, duplexes are typically in tougher neighborhoods, and can be challenging to manage - keeping and retaining good tenants.  

I talked to my attorney about something similar whereby I owner finance a property to an Owner occupant and have property on land lease or retain partial ownership.