Then personalizing an individuals RE short term rental data with functionality tools similar to what AirDNA and Mashvisor have.

When you say, "track each property within its own class for accounting purposes," I assume you mean, can you track properties individually or only grouped together?  

Is there a possibility that it can be sold out seperately as a individual units later?

Click the links below, give them a read, and share your thoughts in the comment sectionThe first will help you avoid getting overwhelmed with the amount of info on BPhttps://www.biggerpockets.com/blogs/5868/52761-the...The second will help you get your investing plan on track:https://www.biggerpockets.com/blogs/5868/52743-im-...and the third will help you find the best agent to assist you when you are ready to make a purchase:https://www.biggerpockets.com/blogs/5868/52724-im-...I hope you get some value out of those.Feel free to check out my other blog posts, and if you have any specific questions you can reach out to me via private message I would be happy to help.

An individual helper could possibly help you keep organized depending on their skills. 

This is entirely going to depend on their individual lending criteria, no general answer is going to do it.

Account Closed On top of what Bill said, you can find a friendly agent who will take you as an assistant, allowing you to get MLS access (you just pay the MLS dues ~$55/6months) and even go to ABOR classes.

BF/GF or roommates) do each one carry individual policies?

If it's a private individual that you're pitching to, I'm certain they will want to see more and something different than a hard money lender or private lending company. 

The problem is the amount of conventional loans that an individual can have is limited.