I have been involved in property rental for about 30 years and have been a software engineer for nearly 20 years. 

I’ve had my eye on medical device sales and software as a service sales for their high salaries + commissions.

You are one surprise (like finding mold which is common in climates where it rains a lot.....like the Seattle area) to be in the red on this deal.First, you might not be doing your comps correctly...or maybe you are but there isn't enough info for us to tell for sure.

I currently use no software.

Make sure you educate yourself on the local landlord-tenant laws and just use one of the many landlord software companies out there to streamline the rental process.

Awhile ago i researched a lot of property management software platforms.

I have a bookkeeper using QuickBooks for me for our 7 single family homes.  I find it difficult to understand and hard to track true cash flow numbers.  Does anyone have any recommendations? Does your bookkeeper easil...

While I was homeless, I made my way to Mexico where life is cheaper and I began self-teaching myself to become a software engineer.After I felt had strong enough skills and confidence to enter the software industry, I came back to the USA to find my first job.

I self manage, use the same software that Michael does, and it’s very easy.

I suggest getting a bookkeeping software such as quickbooks.