I joined after the 90-day challenge webinar to purchase my first rental by the end of 2018; still haven’t locked-in on anything yet. 

Challenges?

If after a few tax seasons you feel comfortable handling it all on your own, then feel free.

Also, from your experience how many management firms handle their own bookkeeping vs. hiring out? 

The challenge is...

If you are sure you are up to this challenge press on.

Do you think I should keep everything DIY (ie turnovers, listings, etc) or give it to someone else to handle?

These types of properties typically only trade when the market is nearing the top, making it a challenge if forced to sell.

You need to handle your current finances before you try handling investments and risk.2.

But it shows how important it is to run a professional business from day one: have a buisness name, a business address (I have a UPS PO box with a real street address) and handle yourself like a company would.