We want to ensure that our financial statements maintain analytical value, but we don't want to make the bookkeeping so tedious that it never gets done properly.So, now the actual question(s): 1.

You are an analytical person, which is what it takes to be successful in real estate, and therefore you are looking at this particular situation as a black and white cost.  

It seems we come from overlapping media/tech/analytics backgrounds and I know just how hard the NYC grind can be.You've got me researching self directed IRAs!

There's a lot of high level, analytical greatness in this thread, but one thing to consider is the following criteria to even get to these places:  @Shriraj Shah1.

At the same time be very analytical of your numbers.

For me personally, it says we are lucky that we still have a lower entry point then most folks markets.If we jump in and really become bit more analytical.

They'll give you neighborhood and property analytics to tell you the top neighborhoods and properties to invest in, projected cash on cash flow, cost assumptions, seasonality trends, occupancy rates, pricing, etc. 

The real estate data in this post is leveraged by market research reports from CoStar Group, the leading provider of information and analytics in the real estate industry.

Marriott and Hilton have access to in-depth data and analytics that they use to justify building a hotel, so if they build one, you can siphon off some of their customers with your STR. 

I now have some workable formulas now though and have exercised some analytic muscles.