The extra cost is typically well worth the benefit. 

. :)   I'll likely do the HELOC and not worry about the extra taxes on gains over $500k when I finally do sell someday. 

I don’t want to underutilize the equity on this property so I feel like taking out 100 grand on our Primary where the rates suck already and it will only cost me an extra 600 or 700 bucks a month. 

Remember to always budget 10-25% (depending on age/condition) extra as a buffer.

We will take the quick deal any day over making a few extra thousand bucks.  

I was a foster child who put myself through college on my own, and I have relied on some good friends for a place to stay as I grew up, which has motivated me to create a better life for myself.I have done a lot of research on real estate, and from my perspective, it seems as if wholesaling, which I feel my sales skills may help with, would be a good place to start to make some extra money to speed up the investing process.

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

You would build equity in your own property and could save an extra $2,000 a month.

For example, if you are in a secured position and invest $25k and can get 10% per year at $2500 or you can get 15% unsecured which is $3750, are people willing to risk the extra $1,250 a year where you could lose all of your $25,000 investment compared to being secured where chance of losing it all I would view as astronomically lower?

"Separation" may not be possible, but I'd like to think of an LLC as an "extra layer" of protection, although you're not completely isolated from risk... just makes it harder for others.