Next, we are looking for a good book keeper to help with depreciation, cost segregation, and Real Estate Professional time logging.

Besides the bookkeeping files from my PM, what are other things I should be preparing and filing to get the best tax benefits with REI?

I am planning to hire someone part time (by hours) and get some help on book keeping via virtual assistance, but would like to hear some inputs from those who have done it before.

What do you use for bookkeeping?

I do often recommend a separate property management LLC, especially for clients with a large number of rentals or using the series LLC as it helps with bookkeeping.

Now, we only opened one account for the SLLC, not multiples - for all I understand and was advised by our asspro lawyer, the requirement is for clear accounting/bookkeeping (being able to account separately for each children Series-LLC and/or asset), not for a bank account for each of the childrens SLLC.I was not aware of any special treatment of SLLC from banks....but I did experience vastly different responses from bankers and loan officers based on the question asked and their domain of expertise (or ignorance) on various other subjects before...so, if you don't find the solution to your problem, change the person you ask or reformulate the question...might be surprised how many "professionals" know only their small yard for answers and tell you is not possible.

I’ve had great success hiring offshore talent in a variety of roles: property managers, project managers, administrative assistants, interior designers (more on that later), bookkeepers, etc!

I would also prefer to have software that's cloud based because I have multiple computers and do my property management bookkeeping while traveling.I currently use Google Sheets to track all of my expenses, mileage, rent collections, etc. and I feel like I'm capturing everything, but it doesn't create standard accounting documents and reports.Any suggestions on software?

It will sharpen your landlord skills, your book keeping skills.  

the benefits of mgmt and bookkeeping being in the same place is HUGE.As the number of doors grows much higher than that, I expect we'll switch to something like Buildium - more overhead to handle financials, but I would think the lease mgmt and turn process benefits and tenant portal features would outweigh that overhead.