It's not an easy process, but with the right team you can make a complex process not turn complicated and be really satisfied with both the journey and results.

Your property expenses will need to be divided between business deductions and personal deductions.House-hacking will also complicate your taxes if you sell the property.

It's a pretty complicated roofline and think it's going to cost me a bit to re-roof it. 

We ended up not making an offer on this property but got to know the selling realtor well and brought him on to help us find a property that was less complicated for our first investment.

It could also be as complicated as one of the several smart locks that you can manage remotely or maybe even one of the pager systems that calls to the units.

It sounds complicated.

Sellers have a good idea of what they want, so unless your offer is complicated or you're asking for a lot of concessions, they should be able to give you a response fairly quickly.  

As far as tax return prepartion, it depends on how complicated your tax return is. 

But if there are court proceedings and situation is complicated, I would get in touch with the lawyer representing the seller and see if he is willing to share any details.

Once you have a complicated structure, besides other issues (IMO) that it creates, one of my main considerations was, you are cornered and limited by who can help you for tax planning and preparation, becomes a burden overtime.