Not to mention I have at least 1 relative in each of those trades will to lend a hand, so the first few rehabs shouldn't be that bad. 

That's the trade off stubborn Sellers should expect if they make "sight unseen" condition of the purchase.  

But, that is not always the right answer and you should speak with someone familiar with your personal situation to get advice specific to you.As for the S-corp issue, you will want to look into the tax consequences of holding real estate in an S-corp and upon distribution.

There are averages that properties trade for in certain areas for the different types and classes of property but at the end of the day it's really what works for the buyer.

@Matthew EwaldFor a payment to be a deductible expense it has to be necessary, ordinary and reasonable in your trade or business.Tools for a rehaber/flipper is an ordinary, necessary and reasonable expense and therefore should be deductible.It also looks like it can be currently written off instead of depreciated.

Due to legal restrictions (search for Dodd Frank law) there can be very negative consequences to how it is structured.

Think E*Trade or Fidelity with different paperwork.

I'm a software engineer by trade, and I'm enjoying the academic approach to analysis that this book brings.

The construction trades are hard on the body, so I am very interested in rental property investments as a way to transition out.I am looking forward to reading and learning as much as I can from everyone here.

You should have the intent to hold the replacement property for rental use, appreciation, or use in a trade or business.