Owner occupied future flip strategy

[Cheri Castro]

I found a home that is move in ready; Minus the roof which is 21 years old. The listing is a 3/2, granite counters, wood floors, tile kitchen and bathrooms. Huge screened in lanai in a prideful pocket neighborhood. Great starter that's move in ready. Its listed at $269,000 "knowing the roof has reached its term".

I plan occupying this home for 2 years and then renting out. I'm currently a w-2 employee and so is my husband. I have saved enough money to pay my bills and portion of the mortgage for 1 year. I also have $50k in savings and $20k in a 401k. I plan on converting to a 1099 by July and going 100% in real estate investing and a working licensed agent in the state of Florida.

I want to grow my portfolio and find single family homes or multifamily with minor renovation needs and rent out.

Question: My plan is to rent it out in about 2 years. Do you think its better to pay for a roof cash? or roll it i to the loan? What strategy should I use?

What is the best strategy to use?