While finding a local CPA is important, consider the option of working with remote professionals who specialize in real estate and small business taxes.

By a professional estimate I mean having a contractor bid the work, not just me estimating the jobs. 

You need a skillset that you can manage tenant's expectations and enforce the lease with a professional but firm manner.

If you're certain the type of renter you're going to get are traveling medical professionals, you know they're on short term contracts (typically 13 weeks).

My ultimate goal is to save up enough money to invest in a fix and flip property(which my family has been doing for a while) and live in it, until I rent it out and use the equity for another home.For any real estate agents or professionals in general, how do you find consistant deals?

The chart of accounts is structured around the Schedule E, so you simply export it and send to your tax professional.

Scott very professional . 

HI,I was curious to hear from other professionals, when you have a tenant for a couple of years, and then he wants to add a new person to the lease, what steps would you take?

Readers should seek professional advice.

-> Besides doing your market research, i strongly advise that before any purchase or offer, that you hire professionals to help you in the process.