He had also done bookkeeping , const and mgmt.

Use portfolio to gain financial independence with cashflow.Keep process as hands-off as possible with property managers managing homes and a CPA and bookkeeper managing taxes.Consider apartment investing and fix & flips in the future.Here is what I am looking for with homes 5-10:Grow in my current markets with my current teams.Explore a couple of more markets (I'd like to get into Orlando).

My accountant recommended getting a bookkeeper at least to help a bit this year as I’m acquiring more properties.

One reason is that the bookkeeping can be a nightmare. 

It is relatively easy to use and as you scale, you will have no problem finding a cheap part-time bookkeeper who knows the program.With that being said, I advocate to my clients any approach that allows them to capture complete information in the manner that is most workable for them.  

Our bookkeeper was not impressed with us.  

I believe my tenants find it as a convenience, actually.I use many of the features that RentRedi provides, including: Unit listing services (can be free or paid), tenant screening, tenant background check (tenant paid), tenant payments and basic bookkeeping (but not maintenance and accounting).

If you have a 1 million dollar umbrella that is usually a bigger target for a lawyer go after than personal assets of under 1 million dollars.There are other things to think about as well.You can't get a convention mortgage with Fannie or Freddie under an LLCYou will have to transfer it into the llc name after purchasevery unlikely but could trigger the due on sale clause in a conventional mortgage on a single familyMake sure to have the liability, fire and title policies done correctly so you are covered after this moveAlso to make sure that you don't break the LLC protection you need to be very precise with your bookkeeping, and keeping up with the llc documentation.LLC also could up your expenses and complexity  if you are doing separate ones for each propertyDon't let the LLC thing hold your back from purchasing your 1st rental property. 

Which is what I personally did I had 350 of these I sold out last year actually a year ago to the day and my partner that took the portfolio decided to out source and it's been a challenge. and I see you have come to the same conclusion .I also own A class rentals in the same market and my bookkeeper manages them from our Oregon office no problem.

I also take accounting, book keeping and business theory courses whenever time allows.