The roof is in dire need of replacement as well as the windows and all mechanicals.

This seems like a very intensive way to document a business that's only anticipated to net 12k a year per property, but I suppose the burden would seem less dire as the years go by and properties are added.

Right now I wanting to move back into the smaller unit and rent out the main house I'm currently living in so I can command a higher rent for the larger unit so that I can start aggressively continue to pay down my HELOC.Another reason I want to get back into the smaller cottage is because it is in dire need of some major renovations like new siding and windows, etc.

The downsides, though, is that the agent may not be able to submit the offer as quickly as you can in these informal cases, and the agent's commission might/will cut into the potential profit of the wholesaler, so that's a factor.Either way can work, and the better your personal relationship with the wholesaler the more strait-forward the process with be without the agent. 

It's not hard for her to reduce this gift amount from her lifetime estate exemption, but consequences are dire if you don't.  

I've heard dire predictions every decade since the 1970s saying Social Security won't be there when I need it.

For most (not talking about dire poverty and such) this is a discipline issue. 

Even if it's in the $100,000-$150,000 range, I'd still trade places with you.There are millions on millions of people in your shoes who, like me, will spend year after year after the age of 31 dead from the neck up about money, unaware of how dire their financial problems are, unwilling to change.

I was raised to believe the desire to have money was bad although it seemed to be the thing we always seemed in dire for most.

But im not in a dire situation to have to do that at the moment.