There are a few elderly people that don't have internet and I'm not going to force them to drive to my office to fill out a little form.Rules are rules, but they should be reasonable, justifiable, and (rarely) bendable.

It's an internet forum so this will happen sometimes and my views are not a statement about whether or not your advice is sound! 

First step would be to have a conversation with the contractor and lay out clear expectations, scope of work and timeline and ask him if he can do it and what it will take to get it done.

The layout of the house is horrible too, it’s very closed off, disgusting rug in one room.

Maybe I'm just lazy, but the thought of paying utilities, cable/internet/cleaning/lawn/short term property management fees, and not to mention regular maintenance  and then you have to budget for the winter months.. sounds like way too much work for me!

Literally tens of thousands of very similar duplexes were built in Cleveland and the inner-ring suburbs the two decades preceding the Great Depression, typically with two full-floor flats of nearly identical layouts on the first and second floors.

Lots is written on the internet about it, and there are a lot of variations of how it goes down... but the gist is what I have written.Randy 

Remember, this is a marathon, not a sprint.Realtor: While they're extremely important in the process, you can't make offers without knowing your construction costs, again, assuming there's a value add play.While you can certainly find people to fill these roles over the internet, it is very important that you go there and perform your due diligence in person.

My goals for keeping it as a rental unit would be to:1) diversify investments to include stable, income-producing real property2) gain experience as a landlord I'm confident the property would rent, but I'm concerned that a historic Trinity might require more time/money to profitably manage (vs. a more contemporary home), because of the age of the property and the quirky layout and maintenance needs. 

There is high speed internet available, and its 4 minutes to the major highway and local supermarkets.I am trying to evaluate the feasibility/profitability of this project.