How about deductions, will occupying the property alter what I can claim?

Both have their pros/cons.The journal Square area is good and you can get into NYC in under 25 minutes.I think the area has already experienced significant price increases over the past couple of years.Live-in-flip is good cause you are looking at a property that needs to be fixed up which can translate to a cheaper cost compared to a house in excellent shape.You are also eligible to exclude a portion of all of the capital gain if you live in it for 2 years and then sell.You would need to keep track of all the repairs/improvements you make to the house.A con would be is that the house has to be in habitable condition prior to purchase otherwise a bank won't loan on it.

Agree totally with @Matt K....this is the first really good advice I've seen on this site in a long time...Foremost, markets exist in many forms and no two are the same (even in the same neighborhood)...if you're buying duplexes then looking at Marcus & Millichap reports is a waste of time...and CAP is simply an estimate of what investors are willing to settle for...would knowing that your target area is only producing a 4 CAP alter your marketing to sellers as you work on your next acquisition of a deep discount deal...perhaps on a purchase money mortgage or lease option?...

In Denver this means you cannot alter the exterior of the building and you need the Historic Commission approval.

So my aim, is to translate this advice, into something a little more tailored to my situation.So my question is this...if you were just starting out, but you had a large amount of capital available to you, how would you change/adjust your day 1 business plan/strategy to maximize your results?

Depending on the zoning laws you might be able to alter the property to benefit your potential for rent. 

The swimming pool and other amenities offered did not translate into higher rents.

It does not translate and it is much more fun and educational to do it yourself.

Then translate that into numbers.What I am trying to say is that the story you've told in your analysis is one in which the numbers are the starting point, instead of a derivative of a larger picture.

I never imaged more convenience and organization would translate into RAGE from a tenant.