As we are anticipating an eventual  "cooling off" period, my wife and I are well capitialized enough to take advantage of better deals.

Once you know how much the gross income will be (represented as 100%), surely it does make sense to deduct every anticipated expense as a percentage of THAT figure?

The security deposits haven't covered the damage done, we've increased the rent for pets as well as the deposit to cover anticipated costs.Whichever way you choose, just make sure you mitigate the potential risks.

When the place flooded during hurricane sandy that was a nightmare situation that I could never have anticipated. 

We anticipate the actual value to be higher since the comps were all over the place. 

It will also clearly define you as the tax payer for the property since a living trust as you're anticipating is typically a disregarded entity.

From your other posts, it seems like you just get a kick out of signing up for things or paying for services, all in anticipation of investing.  

With a  3% FHA I should be able to get there (anticipated $15k saved by the time my lease expires).

I certainly had to spend more than anticipated.

However after my showing I think its a much bigger project than I anticipated and likely wouldn't qualify for traditional financing, so wanted to ask the community about how larger developers are turning these big old houses into multiple condos all over Boston.