Before I answer these questions I would suggest more that you talk to an experience real estate attorney who does these types of transactions to take care of your properties now and in the future.
1. How do you transfer ownership of a paid-off property from a person to a business, and is this smart to do?
To transfer ownership for a fully paid off property is mostly changing title of the property from you to the LLC. You will need an attorney though the laws are not the same everywhere.
2. I previously had a bank that would not lend to my LLC and required that an individual be the lendee. Is there a reason for this and manner of getting around it?
Like someone mentioned before buying a property with an LLC is a commercial loan and a residential lender will not be able to let you purchase as an LLC but I have purchased properties and then after the purchase put them under an LLC. But you will still be personally liable.
3. What are the biggest reasons to title under an LLC?
In 2010, I was threaten to be sued by a worker who was working on one of my properties and fell. The property insurance wouldn't cover it because they said it was a lack of maintenance but the house was a rehab. Because that property was in a separate LLC the only thing he could do was sue that property but since I keep every property in a different LLC none of those properties could be touched. The attorney called and offered a measly settlement because there was nothing to go after. If I would have had all of my properties in one LLC I'm sure he would have went for much much more. Also if you have partners, you want an LLC because partners fall into disagreements all the time.
4. What are the biggest reasons to title under your name?
There is no reason to have a property in my name. It's just asking for trouble.
5. What are your personal thoughts and experiences that could help me and others that are still new to this?
I know a lot of people might think having an LLC is unnecessary and overly complicated (it's not once you understand it) when buying real estate but it's really like insurance. You don't think you need it until you need it, and if you need it and don't have it, it's too late.
Just imagine building up 5, 10, 15 properties just to have it all taken away by a greedy lawyer who wants to build an extra room in their house with your hard earned work that took you years to build. It happens everyday. Lawyers offices are full with clients who never thought they would be there.