However, there are also those who would say that if you yourself are an independent contractor and file those taxes on a Schedule C, you are most assuredly "in business" and that you are required to issue 1099s, even though the reporting mechanism is essentially the same as the first example above.So what to do?

You can research it yourself, but I think what you are referring to is actually an advance withholding mechanism on any income or franchise tax that would be due IF there is gain on the sale of the property to the seller.

The extra expense of cleaning up his poor plumbing, electrical, mechanical, drywall, finishes was substantial.

If a contractor can't manage his business in order to get paid after he has completed the job, then he isn't worth his salt.They will give you the song and dance about needing you to have skin in the game so they don't lose out....this is just silly as they have the BEST position to be sitting in with the ability to file a mechanics lien on the property. 

That really will not work for me, because, as you also mention, it'll be hard to get construction done form scratch in 180 days.Additionally, I'm looking at selling four properties over 12 months, so I need a holding mechanism that would sell to the entity buying with 1031 funds.Another issue for me is selling four properties and then buying two rentals with the proceeds. 

While I know there is still research that can be done and questions that I still need answers to, I'm now confident enough to want to jump in and learn through experience.In a nutshell: I currently live in Roselle, NJ and I'm looking to thoroughly learn the real estate markets in North and Central Jersey I'm currently in between jobs but have a career in Mechanical Engineering and will continue this to begin building capital for future REI ventures I have a strong interest in Wholesaling as my Phase 1 strategy.

Also if you can’t maintain the vehicle or do a good amount of repairs yourself, you are looking at costly bills even if you find a good mechanic.

At the same time I am paying for my child's college education to become a mechanical engineer.  

I graduated with a degree in mechanical engineering and took an extended internship, because the company I wanted to work for needed to know I wasn't a dummy.

I do try and take a lot of pictures and make sure to take pictures of mechanical equipment, water tank, and electrical panel!