My families modest lifestyle is paid for in roughly 10 hours of work per week and more than half of that is done at our house (bookkeeping etc.).  

Its better to develop good bookkeeping habits when the portfolio is smaller, so you don't have to deal with a giant mess down the line.

I track expenses in Quickbooks Online and just hire a bookkeeper to handle deal with entering and categorizing all the transactions. 

The core things for most real estate investing are that you need to be able to: - Find Good Deals and Negotiate - Get Good Funding - Handle the Legal, Tax, and Transaction Side Well  - Manage Fixing the Property Properly if needed - Have a Good Revenue Generation Strategy That works for you, the property  and the market you are in (Location and Real Estate Market cycle wise)  - Rent it (as an STR, MTR, LTR, Section 8, College, House Hack etc) Flip or Wholesale it- Have good systems for the longterm and for scaling - tenant and property management, book keeping etc  A Couple  Helpful Podcast Episodes -  Rookie to Real Estate Investor in 90 Days: Meet the Mentees- Skills You Need to Become a Full-Time Real Estate Investor Real Estate Rookie Podcast - https://www.youtube.com/@RealE...   

Another flip was funded by a private investor who saw my capabilities and proven track record (I had also flipped houses with my parents but was more of the laborer and bookkeeper.)

To be completely honest, i only own a tax and bookkeeping business.

I personally use azibo to do my bookkeeping and tax prep, and it's become more and more simple and efficient.

With payroll and the employees already in place in that company I think it would be easier for bookkeeping and managment.

Grandfather had 200 acres and also took care of a number of other peoples hay as well.I also worked in maintenance and construction before becoming a bookkeeper and then a CPA.

So, I would think hard before creating a bunch of LLCs because you will need to manage bank accounts, records, bookkeeping for each of these separately.