Jaren took me out to breakfast and then (probably uncomfortable for him at first) let me tag along all afternoon as he drilled out locks and broke into all their recently purchased properties to do reports and take pictures.

While these may be extremely uncomfortable to ask, they will be taken well if you are truly genuine in trying to help her.

I now have to provide the routine documents  (W-2s, pay stubs,  tax returns ect...)

Sort of your "day-in-a-life" or successful daily routines, habits you've built up over the years that work effectively for you.

Your lender will likely require you to have capital requirements, which sounds like you might not make.If any of these answers make you uncomfortable, think long and hard.

There was also a man in Texas that purchased a dam that surrounded his property,  (you have probably seen it being in your line of work), I thought that was interesting, but of course not very practical on a routine basis, but I wondered if something of that nature could be applied in a similar fashion to hurricane shutters.... i.e. you install hurricane shutters and your premium goes way down and they essentially pay for themselves in a couple of years.

The miracle morning routine is what I do every day now and it has had a huge impact on my growth as a human being and an investor.

The plumber told me that he routinely sees water heaters in Milwaukee go past 25 years without a failure because of the water quality.

But, it seems you're doing the discount flat fee routine.  

My strategy is mainly buy and hold, implementing the BRRRR strategy Brandon and Josh routinely talk about.