(If any landlords are reading this, please let me know if you think this is a deal breaker)I would really appreciate anyone who can give me any advice if you think I should just pull the trigger or not?

Hence, I want to invest my time and educational dollars as efficiently as possible to more rapidly get to a point where I'm actually comfortable enough to pull the trigger on a deal.

I almost pulled the trigger on a 1BR apt in Lincoln Park for $229K but it was just outside of my spending capacity, I would have become house poor and my goal is to buy investment properties in the near future.

You may also be able to take classes that focus on multi-family investing, house flipping and commercial real estate to help you gain base knowledge and give you the confidence to pull the trigger on starting your investing. 

If that first mortgage is current, and you continue to pay it down, the original lender should have no reason to trigger the due-on-sale clause, but this is something that can happen.

My question is if this will trigger a tax event.

David Krainert Hey I started the same way where I lurked for a good while before finally pulling the trigger this past November.

Often, the situation where the house is not habitable will trigger certain actions. 

Hi Bigger Pockets, I am getting ready to pull the trigger on my first property.

When its time for the very big pay day down the road, you'll be glad that you waited to pull the trigger.