As an example, my neighbor added a second story to her home and the contractor gave her an estimate that she agreed to. 

We own a property in the mountains on 2 1/2 acres that has 3 houses with 9 bedrooms and can sleep 24 people.Our second house is on the beach off of Playa Avellanas.

I can second that @Wale Lawal is amazing and knows what he's talking about! 

I had to get a home equity line for about $20K, which put my first and second mortgage at $153,600.

Second, real estate investments generate a return in one of two ways - Cash flow and appreciation.If cash-flow is negative, is the appreciation making up for it?

Many insurance policies also require re-development within two years, a near impossible timeline in a region with the coastal commission, perhaps only second to Manhattan in terms of permitting and red tape.

The second you are introducing metrics to change your marketing that have nothing to do with generating the leads you need, you introduce uncertainty to your systems. 

The second company had a PM contract and due to other reasons we did not continue their services after a couple of months so tax stuff did not arise.

Best thing to do is buy it as a primary or second home and then transition out into a rental. 

Searching through the forums is like my second google, ha!