Getting second mortgage on new residence

[Kenneth Cowan]

What does the process look like to get a second mortgage? I bought a condo in a 3-flat in Chicago in Dec '14. I've been fixing it up for 6+ months and plan on finishing all renovations in another 18 months. The plan is to rent the unit out and move to another home, maybe repeat the process. I enjoy the work in my free time. How do I qualify for the second mortgage? Does the 1st mortgage count against my debt-to-income if I plan to rent? I put 5% down to buy the place, and plan on moving onto new property once I can remove the PMI on the current unit. I have 750+ FICO and plan on having 15-20% for the new down payment. Do I have to show x months of rental income before it counts? Do I have to be able to cover both mortgages with 35% of income?