Your list here includes some things I have not yet contemplated, so it sounds like I should continue the journey towards listening to all of the episodes.

Perhaps I should rephrase it to something along the lines of, "What areas of concerns should I focus on when contemplating tear down?"  

Sorry for all the questions, I am just contemplating if it's better to hire someone at $15/hr to do the leg work or would the software do the trick

But when you're combining sales to purchase one asset like @Ratesh D. is contemplating you've got to be especially concerned with the date of the first sale. 

Before you contemplate those uneven distributions, talk to an experienced REI tax accountant, as there will be some unintended tax consequences, especially at sale, not to mention the complexity of arranging it and potential friction between the partners.

It is generally ok, and on average my tenants stay 2-3 years.  5 of the properties are within 10 minutes of where I live- and the other 5 are about a 1/2 hour away: 3 to the north, and 2 to the east, so they are bundled" somewhat, which helps.I am contemplating hiring a 3rd party. 

So modify Dave's plan D and you still may be able to get at least part of the dream painlessly.If you were contemplating on moving in and then selling vs holding till death. 

This is the move (other than investing in different markets) that I am contemplating more and more as I look at MLS-listed properties around the Triangle.

It automatically does all this when we get a new booking over Airbnb or VRBO.It works great and is included in the Hospitable's monthly fee.In fact, I was contemplating moving over to OwnerRez to start working on a direct booking site but Hospitable works so good I'm kinda stuck.  

The STR which I am contemplating to switch is in a big ski town & does cash flow well.. trying to max it up & not worry about rising expenses in maintainence , read the other day about traveling nurses needing individual rooms & with a huge dearth in inventory for longer term accommodation - there possibly could be a more steadier & higher income stream