Then you could be eligible for a 203k on the next and you would have some good bookkeeping to support the rental income from the first (at least get a tax return filed for 2017).

If the habit is to pay late and pay the late fees each time then as long as they are causing no other issues you keep them.The KEY is that they never go over 30 days as next months bill will start snowballing and they will want to do partial payments.It will create extra hours for you or your property manager to collect and additional bookkeeping.

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

Sharon brings 30+ years experience in Business Administration, Bookkeeping, Accounting and scheduling.  

I am at a stage where I am considering outsourcing the bookkeeping altogether.

Other than that, everything he says should be done by your bookkeeper, if  you are not at that’s Level to have a bookkeeper, following what he says will helps. 

We were using Google sheets for a while to do bookkeeping and Venmo in the early days.

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.

In addition to our property preservation field service business, I also own a bookkeeping business and have investors as clients.This is how I have them set up:Use the property address for the customer, then add each tenant under the primary "customer" as a job.