A transfer of a property, purchased with a personal loan, into an LLC can trigger the Due on Sale Clause; however, a transfer of a property into a Land Trust does not trigger the same red flags because the Land Trust is considered an estate planning tool.

I think I'll pull the trigger on this one and see what happens!

This could trigger it making your entire loan balance due in full, now.

Might trigger IRS issues because it exceeds the gift tax threshold. 

I feel like I’m lacking direction and am nervous to pull the trigger on a property due to my inexperience.

If they are in your LLC, you just quit claim them back to your personal name to do the refinance and afterward, Fannie Mae allows you to transfer them back to an LLC without it triggering the due on sale clause.

Given my current situation at work (time-consuming), I'm focusing on B area units that are turnkey / require light rehab.I've been running the numbers on a few properties that I've seen and with the estimates I've made, these properties are so far from cashflowing that I'm becoming skeptical if 1) I'm doing this correctly 2) there are actually cashflowing properties in these areasMy main concern is whether my expectations are too high and thus will never pull the trigger unless another '08 happens again. 

With real estate the people that fail are the ones that never pull the trigger. 

This  does not trigger the same flags with traditional lenders, and when established correctly can keep your name anonymous from public records. 

I also agree that I need to get some estimates from the contractor before pulling the trigger.