I want to do taxes the HARDEST way possible. (with questions)

[David Zheng]

So in my first year of investing, I've bought 8 properties from condos to sfh, to multifamilies. All are rentals. 7 are in my personal name and the eighth property is under my solely owned LLC

I am literally leading myself to the slaughter because I want to learn the ins and outs of real estate taxes by doing these myself. I have a couple questions before I go through this pain though.

1. Do I need to prepare a separate statement for my individual tax returns and my business one?
2. Besides knowing all current rents, Mortgage insurance/interest, HOA fees, expenses, rents, property taxes, what else should I have ready? Everything I track in Excel
3. Do I just use the appraised value of the property for depreciation? So if I bought a house for 275k (lets say it appraised for 275k) and closed Aug 1, is the depreciation just 275/27.5*(5/12) I read somewhere I needed to separate the building appraised value and the land?
4. Recommendations for the most user friendly software? I used TurboTax and I like it a lot.
5. whats the hardest part about doing rental taxes? Is it just locating the numbers or am I missing something?

Hopefully questions answered here will help with other first year investors with these questions!

Thanks!