Talk to your CPA to go over the specifics of your situation, but in general it makes more sense to have an S-corporation for wholesaling than an LLC. 

Making money on an investment property is not their priority so they are willing to pay more than an investor who wants to actually be profitable on the property. 

I need to exhaust all avenues of creative thinking first and maybe show him by teaching him and pointing him in the right direction, so he comes to his own conclusion that it is a bad deal and then find a good deal.

In fact, when I first asked the group for paid marketing advice, one of the seven figure members told me I should exhaust the MLS and wholesalers first. 

@John SoSince you have multiple homes already, an LLC may make more sense than an umbrella policy (unless you mean those are all personal residence/vacation homes and not rentals, in which case you wouldn't want them in an entity).There are several considerations that can go into the analysis of whether you need an LLC or whether a large insurance policy will suffice.

They seem to much easier/cheaper/most energy efficient than an HVAC on paper. 

Can you imagine how much riskier an empty house is than an occupied one?

I'm not going to list a property when you have nothing more than an illegal contract with a distressed seller.2.

If your project is smaller, you are probably better off working with a local contractor who is familiar with local requirements rather than an Upwork consultant.

That's not worth it to a lot of people who may already be successful and well respected in their jobs, or who recognize that success and respect are closer in the work they are already doing and have experience with than an entirely new industry.