And it occurred to me that by purchasing this property I'll be increasing my monthly cashflow 25% going from 400/mo to 500/moOf course I'm not considering this in a vacuum, I have other factors to consider like appreciation, principle pay down, etc.

The best course of action is probably a HELOC.

ThanksDan there are people who do "Gator" lending which is a guru course taught about this type of lending.

The IRS has a regulation that amounts less than 15K are tax-exempt, of course, this requires you to file a tax return.

We recently purchased our "forever" home together in another county and applied for a homestead but of course we were denied because they found out we had 3 active ones in another county.

If I had been tracking the assets via accounting, I would simply make a journal entry showing the LLC's assets and liabilities going to zero and transferring them to the Holding LLC or the LLC Members. correct accounting only and yes there are bank accounts (of course)

I have reached out to a few attorney's and of course they are saying I would have to put them on retainer before giving advice. 

there are of course more creative strategies to reduce that up front outlay, or recoup your capital, like, say, the BRRRR method. but they are time and energy intensive and certainly not hands-off. 

Of course Morris portrayal of C/D class was a fantasy from the get go..

My name is Rebecca and my husband, Nick Knox III and I have run Captain Save a Home LLC, Brew City REI Club, Brew City REI Training Cafe and Wisconsin Contractor and Handyman Club based out of Milwaukee, WI for over a decade.