At the same time, it is ok to enjoy the fruits of your labor and relax too!

I will be the contractor working with the architect firm to ensure this project goes smoothly.  

I used a contractor that did not speak English.

I am a contractor by trade and understand the costs/processes to build, but I am lacking in how to determine a proper sale price with little data. 

The only reason we have requested his presence while contractor is there doing the repair purely because we are worried that the tenant might accuse the contractor damaged his stuff, etc. later.

I am happy that I did the "extras" because I get to enjoy them now but the ROI is not there.

Varies based on contractors, location, permitted vs. un-permitted.

You will need a great set of contractors, a good realtor who understands investments and a really investment friendly mortgage broker.

The problem I see my clients get into with vacation rental purchases when the intent is to get something they can enjoy as well is that many times they get tired of going to that one spot. 

Real estate is playing big - just hiring the wrong contractor can easily cause us to lose $20K.