I have been so hesitant to pull the trigger on investing in another market.  

I would say that most successful investors aren't pulling the trigger on a deal unless they can get really close to all their money back. 

My wife and I have been researching into real estate investing the past year or so and are ready to pull the trigger and buy our first investment!

I’m ready to pull the trigger.

(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.