The second and probably biggest issue with loan approval is that most underwriter's will spot that the property is leased out for another eight months and will stop the loan from going through as an owner occupied loan. 

So, I get in my car after viewing property, turn on an old BP podcast from 2016, and they immediately start talking about a purchase in Chicago at a 4% rule, and how it was the biggest headache ever and the money wasn't worth it.

I also find that it is challenging to make the numbers work once you add a general contractor to the mix. 

@Ross Flaharty doing a true calculation will be challenging. 

I've found the biggest factor is proper pricing.

My challenge is limited time with the demands of medical school and family.

@Frank Crianza The BEST advice/tips/tricks I can give - I have already given ... research is one thing, but obtaining the financing is another - I have a boatload of assets and a ton of net worth but obtaining "good" financing is a challenge without a paycheck from an employer ... you can find short term financing with higher rates and costs based on the value of the property you are buying, but you will find it difficult to obtain good long term financing for long term long term investments while self employed

NZ is one of the least affordable places to buy in the world believe it or not so the barriers for people getting into their first home (20% deposit) are very high and challenging.

It has helped build a great relationship with the sellers we work with.Just thought I share some of our experiences dealing with sellers.You guys run into some challenges?

Unfortunately hindsight is 20/20  however I decided to do something about it  my first step was to create my own business about four years ago on HR outsourcing and consulting  which increase my income pretty well, however scaling it up has been a challenge, Specifically after I got hooked on real estate.