A lot of this process depends on your laws regarding STR and Mid term leases/occupancy?

Whether you are getting a continuous stream of income depends on the deal.

Always trade offs, especially depending on how long that buyer is looking to keep the property, or refinance.

On an annual basis, the administration is mostly meeting minutes, resolutions, and annual filing of your 990, most of which can be outsourced depending on your budget.

If you are thinking out of state, it really depends.

But I guess it just depends on what you're doing and what you need.

And this does not include the real world issues, namely are you even allowed to convert this property to a four-unit and taking a single family to 4 unit is very likely going to cost more than $110k (but this depends on the actual layout and work scope).

HI @Zachary Sakena putting property into LLC in my opinion depends on that strategy you are looking to implement for next property and if you want to leverage property moving out of into LLC.  

However, I suppose it depends on your situation.I know some people who borrow from their 401k or use an IRA to pull from.

And if you only talking $1-200k it is not a massive initial reduction depending on their basis.