The other county I have someone that goes down and get the files for me.

We use Digb, they also support us with tax filing. 

It contains hundreds of files such as ebooks, checklists and spreadsheets for real estate investors: https://www.biggerpockets.com/filesGood luck.

I file my taxes in Florida and am considering setting up an Investment LLC, a Property Management LLC, and possibly another LLC for short-term and mid-term rentals.

A new tax year is upon me and I'm thinking of buying quickbooks, as it would help me file my taxes and would look better to a lender than the expense sheet of my own creation.Thoughts? 

When I was a more active buyer, in my area I did similar deep dives into the HUD/REO markets and courthouse sale data based on Substitute Trustee filings.

Remember the 90 day rule is from the time your deed for purchase was filed until the time new sales contract is signed from what I understand. 

If I invest a multifamily through a Roth IRA, will I still receive the same tax benefits as I would with personal cash when I file my tax return?

In Florida and in my county, I'm looking at the follow for each LLC:- Business Tax Receipts filing every year- Home Occupation License (may or may not need this for an additional LLC)- DBPR License annually- FL State annual report- Tangible Tax filing (and this one is a B***CH)- And now the new BOIR

After that, think about hiring a bookkeeping firm that specializes in serving REIs.Regarding hiring a CPA/tax pro for tax advisory and/or tax filing, I'd wait until you purchase your next primary and convert your current primary into a rental.