I'd like to convert the basement to an apartment for my aging father but concerned about the costs. 

And I can rent it out quickly.Or to future proof, I can cough up the money to convert the living into master bed, add a bathroom since it next to kitchen plumbing (maybe?).

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: Do you think its better to pay for a roof cash?

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.

This converted to a non financed cap rate of about 8% at closing, then with some swift expense adjustments brought that up to about 11%. 

Yes, when you are ready to acquire the property, there is a planning that can done regarding  what kind of property to acquire to mitigate taxes, but when you are converting already owned property, you are stuck with either more taxes or tax saving it has to offer, you dont have a choice. 

There is a dip in the driveway that leads to said garage and I was hoping to convert to you a makeshift living space for myself.

I'm debating whether I should go through the planning department and convert the SFR into an official duplex with the city.

You just need to understand what your buying, do great due diligence, have a plan incase the lagoon fails (new lagoons, convert to package plant, hook up to city).

Has anyone gone through the paperwork/legal process of converting a Single Family Home into a Duplex?