As @James Wise and others point out; Do the basics.

This is basically a math problem that will depend on both you personal finances & also how much of this is an investment vs you want a nice house to live in4.

It was basically a gut job.

Start by learning the basics, networking, and analyzing deals.

My basic underwriting making some standard assumptions on HOA expenses, 20% down, 7% interest rate, 30 year mortgage, utilities, supplies, and maintenance costs shows a loss of about $22k per year if you are self managing.

I'm currently in the market for a Tax Pro that can assist with my relatively basic returns and continue to assist with a tax strategy moving forward.

When your rental income is 1.5-2x the mortgage payment - as is typical for highly refined STR strategies - they're basically not concerned about the mortgage payment.

I bought 14 houses basically for free by harvesting the equity in my houses by doing 5 cash out refis.

But I think you are asking for a standard timeline for a basic transaction @Kiryl Ulanovich. 

Most will require basic documentation such as a complete loan application, ID, Entity Docs, and 3rd party contact information.