The 100% bonus depreciation from TCJA is insane, even factoring in just a few items into my segregation study can easily amount to tens of thousands in year 1 taxes. 

Bonus points if it is a neighborhood that is poised to appreciate.  

Likewise, income from tips has to be treated the same as bonus, commission, and overtime, meaning we can't count it until you have a two year history. 

Bonus for getting them at resorts with central reservation and booking.2.

On top of that, it is a 5 bdrm home so I'm thinking I'd get those looking for a 4 bedroom (and would consider the 5th bedroom a bonus).  

There are endless possibilities for this it seems, depending on your layout and how you generate more income to help offset the cost of equipment if you needed to- keeping in mind your equipment would be deductible.Thanks to the Tax Cuts and Job Act of 2017 (TCJA) you’re likely going to be deducting expenses like this at bonus depreciation in year one (verify with CPA) Overall if you’ve gone over the numbers and they make sense to you, there are numerous ways to go about generating capital to invest in new equipment if you need to.

I'm curious if any of you are aware what types of "improvements" to raw land are able to be used (via cost segregation) for bonus depreciation? 

From the description it sounds like there may be an opportunity for you to rent the 4th bedroom and live in either the basement or bonus room?

I have an idea of how to do it: -lump the 5 year items together in the assets worksheets, depreciate as needed and select bonus depreciation -lump the 15 year items together in the assets worksheet, depreciate as needed and select bonus depreciation -subtract those totals from the structure value, so that I am not double dipping.  

@Joshua J Cawthorn I can let you know what the unit density is based upon zoning....there are also several varying densities based upon several differing density calc's for certain overlay zones and/or bonuses.