Would you recommend hiring CPA for planning right off the bat for first property?

When investing locally, it helps to network with as many locals in the industry as you can.

Confidence.Real estate confidence can come from networking with other real estate investors at meetups and realizing that most investors aren't on social media.

*I am not a CPA, tax professional or a lawyer*I cannot give legal advice, so all of my advice is illegal advice.As far as I know, section 469 of the tax code is what allows for the "STR loophole". 

Make sure to work with a realtor who is also an investor who can easily plug you in with their systems and network of lenders, GCs, PMs - someone who will have your best interests.

And your CPA has no bookkeeper referral to give you?

Though the leap looks easy on paper, it's scary when you try to put it into practice.I’m here to build my network, learn from experienced investors, and get insights on navigating the world of real estate.

Like @Jonathan Greene said, networking locally is a key. 

Not necessarily - you can network with wholesalers and investor friendly agents to help you find deals, your learning curve will just be knowing how to evaluate the deals and if they can make sense for flipping or having to hold afterwards.2.

Liam,Let's Connect add me to your Network.