This seems like a fairly easy exercise in comparison to a large multi-unit property with land and lots of improvements.

I have an option to purchase a plot of land in Los Angeles at an attractive price but I do not have the funds to exercise it.

Is the cost segregation exercise worthwhile given the purchase price ($2M)?

I do have sample of two cities, Indiana city with zero appreciation and meet 3x rules and/or Wisconsin property that has CF as well as appreciation.

Written by attorney investors, it's full of practical advice about the management of investment property, has sample forms that can be edited, and - most importantly - tells you what your primary state laws are and where you can read them.

Cross reference with employers with higher education off linkedin (use an API), and see if there's a correlation between housing prices in districts which are being gentrified, school ratings over that time period, and housing prices (in fact maybe there's another correlation between if these employers work for recently IPO'd companies and are exercising fresh options to purchase real estate).

Analyze markets, analyze trends, and exercise a strong sense of financial acumen.  

Hi,I rented out a room to two friends over the past 1.5 years and it all went well so I never had to really exercise evictions/late fees/ any other nasty things.

You would like to be able to do the things you want (travel, take classes, read, exercise, visit friends/family) without the constraints of a 9-5. 

But how do you project annual occupancy with a few month sample especially if the market has seasonal fluctuations?