The problem (as you have cited) is trying to understand what you need (you don't know what you don't know), where to get it, qualifying its source(s), and the validity and usefulness of all that.Pardon me if I've gone into this too much, but I meet many people with the same concerns that you are voicing and this is offered, as much as possible in direct response to your post.Please feel free to contact me if you have any comments or questions. 

Check out FilePlace, where user-created forms are available for free.

ESPECIALLY if you’ve lived in any of them 2 of the last 5 years and can take the tax free gain. 

Most of the information is out there for free. 

This home is not a luxury home so the insurance route seems overkill.2) Buy a worry free waiver and add it to the booking rate?

Quote from @Zach Howard: First of all, feel free to make any and all comments you wish; there's no need to sugarcoat anything.

So I am hoping to pull the trigger on a fix and flip in the coming month or two so I can finally go from 0-1!

In my area they will do that free if we agree to hook up at least 2 appliances to it.

2) Subsidizing rents:- S8 and other programs statisitically only train tenants how to be dependent on the free handouts.If you really want to make a difference, try basic financial education for tenants and the financial demographic they come from!

Leveraging business credit for a real estate deal, especially if that credit is only interest-free for a short window, isn’t automatically a bad idea…but it’s definitely not for everyone.