I have a rental in a large lot - easily enough to subdivide to 2 parcels, plus the house sits at the edge of the lot.

Okay, Rand Paul has spoken up, but the rest are just part of the "happy machine" to keep spending our money (while keeping a very large cut, kinda like a mafia loan shark) to give to ourselves to "make us happy".

We're just a small company and I figured I would take a short cut by asking. 

I would just be cautious about taking on such a high cost basis this late in the cycle because when we see the next buyer’s market it will probably cut into your equity.

The issue that I'm facing now is whether I want to pull it out against one of my rentals or on my primary.I have found a bank that will allow me to borrow as a second lien on rentals but their rates are higher than what I could get when just doing it against my primary.What I'm most worried about is what happens in a worst case scenario, should something drastic happen in the market.From what I understand, using the money against a rental doesn't necessarily provide much more of a safety blanket in case things hit the fan because if, somehow, the HELOC lender can't recover their money, you'll get sued anyways.

I know that it's not nearly as clear cut as that but that was my general plan.

Even if you have a "perfect" house, it will not rent if not priced correctly, OR you will be overrented (yes that is a thing) meaning you are leaving money on the table.Marketing is also big - Again depending on the area you want to be on as many relevant channels as possible - Airbnb, VRBO, Booking.com, Zillow, Furnished Finder etc and have a direct booking strategy for repeat guests to cut out the middle men.Best of luck!

My goals are to provide financial freedom for my future family and establish a sustainable safety net if physical limitations prevent me from retiring from my current W-2s.

Unrelated to HOA but if homes won't pass the safety engineered designation, who demo's house and haul off and when does HOA or city make owner to remove?

I’ve definitely seen this, or rather one part of the bank saying it should be fine and the back office part having a different trip wire for return.Doesn’t mean the tenant didn’t cut it awfully close but I’d let it go as long as it was resolved immediately and the tenant paid any overdraft fee.