Your title implied that you might not do that step.To your question, I think the first factor I had always taken into consideration is: do you live in the house?  

I have one property for sale right now just because i want to diversify into another opportunity outside of Real Estate and home price is up considerably from where I purchased it about 5 years ago. 

@Jared HottleThanks Jared, I appreciate the list of considerations.

Heard about pine quite a while ago... sometimes it takes me a while to pull the trigger but finally am on this one.

The fha 100 mile rule will be triggered whenever you try to vacate your current primary and also trying to use the rental income to qualify.However, this 100 mile rule can be exempted for the following rulesRelocationIncrease in family sizeVacating a joint owned propertyNon-occupying co-borrowerIf you are not trying to use FHA on your 2nd house hack, you can use conventional and the rules that I mentioned above will not be a concern.

What are important considerations & challenges? 

What considerations should I have if I add this? 

@Hunter Kennell@Jay Hinrichs certainly would be a credible referral as someone who's been in the business for a considerable amount of time!

To me the primary consideration is ALWAYS business, as opposed to taxes.And here is why business interests dictate the opposite of what these gentlemen suggested.a.

Fix and flip loans are cheaper and considerably easier to close.Smaller building projects are often funded in cash on a phase approach.