I believe the advantages of using Cloud services outweigh the small risk..

@Holly Collins - these are 2 different value propositions here.1. cashflow (aka rent)2. resale valueAgain, I think this depends on what your personal real estate goals are and specifically where the property is located on the peninsula.I personally prefer cashflow value because I think it will far out-weigh any negatives when you go to sell in a few decades.

Will these costs outweigh the benefits?

The successes far outweigh the failures.

I am sure we are taking about the significant appreciations  and benefit of tax saving outweighs the some of the downside of holding on S-corp. 

To me, however, that convenience was outweighed by the negatives I described in my earlier post.

There's pros and cons to it but for me the pros heavily outweighed the cons. 

In ohio you do have to pay interest on any amount above a one month security deposit, but rates being what they are the cost is minimal and far outweighed by the benefit of actual notice.

The monthly savings typically outweigh the additional insurance cost.

However, you'll only be pushing off the taxes on the appreciation, so even if you were actually saving the money, it would take a long time and a large amount of appreciation to outweigh the costs associated with selling and buying.