I know I will learn along the way, but it is slightly overwhelming to think of venturing into something 'brand' new to me trying to get as much right as possible. 

For most of his lifetime he has only seen appreciating markets, I am not sure he has truly accepted that we are in a "brand new" reality and the future may have little to do with the past.

Sounds like a good plan you have to get the test done while the material is fresh in your mind.  

I just went though the whole "call everybody process;" hence the numbers are still fresh.

So to make a long story short, I was driving my daily commute home and saw a branded sign in front of a home that mentioned they were rehabbing the home to make it a better place an improve the community.  

Because the costs of engineering and holding, combined with the diminished value of the existing property would exceed any profit realized from splitting the lot up.We decided to focus on a remodel that would add a nice first floor master suite, open concept and brand new mechanicals. 

So, I was thinking of just riding it out until I get a fresh tenant, then raise their rent considerably until they move or sign the lease.Thoughts...

As far as those other things, everything in the new unit is brand new so hopefully i dont run into those issues right away. how do you go about calculating that when getting your property?

I am offering you a chance to start a new, fresh chapter of today, instead of hoping to do it in 3-4 months."

Aaron is obviously brand new, and comments made are directed to the OP in that light, I seriously doubt he's got 12 employees and starting off offering a 401K.