It's when things go wrong or get complicated or challenging, that you will realize you made a good decision or not. 

Any complicating factor is that many accountants do not specialize in real estate and may not be the best fit for what you are looking for.

If you sell a house-hack property, you sold two properties, you sold an investment property and sold a personal residence.The sale of a house-hack also gets complicated if you sold a SFH or a Multi-familySection 121 exclusion may apply to the sale of the personal residence.Best of luck.

Any historical society complications?

I moved our taxes to a CPA before we had rentals because some other elements were getting complicated.

(expensive and complicated).2.

To furnace complications and more.Ultimately, the property is under contract currently with a reasonable path forward and I have learned a lot more during this process that no books or podcasts could have thought me.

This opens up a whole new level of asset protection, going from basic (least expense) to complicated (expensive) very quickly.  

Another person gave an example that was so overly-complicated and heavily branded (whole-tail to a retail to a donkey-tail with a gator covering the entrance fee… lol), I had trouble even following it but once we dissected what was going on, she could have just taken a hard money loan and done a flip and made more money, plus it would have been a lot more simple and less risky. 

It's not super complicated.