Even ignoring the 'theft' risks, you have gift tax return exposure (and use of lifetime exemption), transfer taxes, no basis step up involved with gifting the property back and forth, probate risks if the 'buddy' passes away and didn't update their will for the property. 

The only restriction is that you must execute a direct trustee-to-trustee transfer. 

In the event I'm a big fat failure they can foreclose by doing an SPE (Special Purpose Entity) Transfer of the LLC in which they become the managing owner and it doesn't affect me personally.

The goal with paying it off would be to jump the mental hurdle of owning a property free and clear, start an LLC and transfer the title into that LLC, and then to have a property that we can HELOC against in order to have the flexibility to make cash offers so that we can begin making LLC purchases more easily rather than titling in our own names.I'm certain that plenty here would advise to continue rolling the money into new properties, rather than to pay one down, since owning the house free and clear would provide about half the cash flow that we could get from down payments on two new properties, however my wife (in particular) and I both like the idea of simply owning one property outright and then using the above strategy moving forward. 

This will be a lateral transfer for my day job and will put me within striking distance of (what I think are) my target market(s).

The Board decided there was excess money in a fishing derby account and transferred $500 out of it and into charitable fund.After contacting board president with my concerns.

The county development office would be a good source for permit and plat history to get a sense of quantity, and individual property cards (and recorded deed transfers) may give you a sense of price direction.

You should get tested for any blood related diseases that could have transferred to you, there are more than you think

The previous lease converted to a month-to-month and it transfers with the sale of the property.

Disadvantages: If you are planning to use an external accountant, it hassle to transfer the data back & forth and also since your data is housed in your computer, there's a risk of losing data in case your hard drive failed.