My taxes are starting to get complicated and I am super happy to be working with @Steven Hamilton II.Just to clarify are you looking for an investment property or would you consider doing a house hack? 

You’ve got a lot to wrap your head around but none of it is very complicated-you just have to learn enough to get started, you’ll learn a ton doing your first deal.

Am I overlooking possible complications?

Don't know why this is so complicated.

Dealing with investors adds a layer of complication to the deal.

This caused complications and delayed our closing (which cost me $1k to the seller).

The other issues are that you normally need positive income and depending on what state you invest/live in, it may need to be added back for state purposes.Bonus depreciation is moreso available for residential real estate investors but only certain items can be eligible for bonus depreciation.To add onto all of that - even if you can take bonus depreciation, it may or may not help you in the current year.Yes, taxes are complicated.

Investing in a flip is complicated and messy for a SDIRA. 

Even if you were local, this is always complicated, even if you have a hundred deals under your belt, and many investors never really do it well.Now, as I said earlier, there's a second aspect to your question that no one's talked about yet in this thread.

., my personal auto), or should I keep them separateSorry such a complicated question.