A lot of DIY tax software is good, but it does require a decent understanding of the tax law to ensure that you are not missing big tax deductions.I would consider reading information that CPAs put out for free on their blogs (you will find a number of good articles through a simple google search). 

I currently work as a software developer in Toronto, and after many years of long hours and late nights, i started questioning whether i wanted to continue this path into my 30's and 40's (currently 28).

Curious if anyone has used the software?

I was hoping to get some answers on some great RE resource websites as well as software you all use.I've done research on a few, just would like to hear some opinions from people using them daily.

I just went to tax lien seminar and they said if I pay the $597 I get 3 day class plus free software.

If you would like, we could go in on the software together.

https://screencast-o-matic.comScreencast-o-matic is software I sometimes use in my full time job in the field of education

I did make assumptions on insurance but I feel that $800/year is very low and that you would have 5% of rent in lawn care, professional fees for tax software and other, and a small budget for small repairs. 10% for property management is the norm until you are managing 5+ properties then you can start to get some breaks.I hope that you are able to make this work for you but it will be tight even with your 30% down payment which is a lot of cash to tie up.

I am looking to switch my software to something centralized.

In my software, it's literally a button click and a confirmation.