Very simple as Chris notes its just an up front agreement..

Once your build contract is signed and the build deposit is received, it's not just a matter of filling out some simple paperwork to start the permitting process.

Nate @Nate Marroquin   You can use the income from your tax returns on the current rental adding back your paper loss (depreciation) and add back the mortgage interest, property taxes, home owners insurance deductions on your tax returns. 

It's really simple; when ya don't know what to do or how to do it HIRE and employ those who do. 

Even simple things like making sure each photo on Airbnb has Alt text and that is fits into their SEO categories, I was surprised that more people weren't aware of it. 

Hey Hey @Veronica Mitchell - The most simple advice is to follow the CTA trainlines.I personally love the South East Corridor of Chicago which has Bronzesville, Kenwood, Washington Park, Hyde Park, Woodlawn, and South Shore.That area will continue to be gentrified because you have the lakefront and CTA trains.Others mentioned NW along the Blue and West along the Pink, Green, and Blue lines.

On paper I am only expecting to lose $1,200 for the year (assuming no cap ex expenses since I renovated everything recently).

Keep it simple, transparent, and aligned with your long-term goals.

As I studied earlier, the first thing you should do is marketing, then get a call and do a property analysis to understand if it's profitable for you, then meet with the seller and sign all the necessary papers, then if there is a debt in the bank we do a reinstatement quote, then do a title search to check if there are any hidden debts, if everything is fine we look for an investor or flipper and sign an assignment of contract with him and wait for closing to get our money.

Beyond that, every city I have been to has rough areas where "cash flow looks great on paper" and "nice areas where appreciation should be great".