Cody,There was a time when portfolio loans were definitely the way to go, specifically when rates were at rock bottom and you could bundle as many of them at that rate as possible.

It sounds like you already have or are looking for a very specific property type (studio or 1/1).

What specific questions are you looking to confirm? 

I'm new to this industry and would like to learn, grow and collab with some of the best minds in the biz!

Unfortunately, recent regulations have made it so that I can no longer STR in my neighborhood.

Lot of people may leave the industry.

There is obviously a formal lease, and we also supplement with a room mate agreement which outlines the more specific things like overnight guests and expectations in dispute resolutions/ cleaning/ care for the home and appliances, etc.I haven't received one formal "LL request" email yet, other than a formal 30 day notice in the event of a move out, which is usually after they've come talked to me in person about it to begin with. if there's an issue, it tends to be pretty limited to "hey, we have this shower rod falling off"... which im usually here to deal with (and tbh most of the time they like to fix it up with me), and it doesnt need to turn into a big thing. as for keys, i have the house on a yale smart lock, so 'handing over keys' is just official move out, walkthrough of the room for damages, and then I can delete their access code and access to the smart home systems without having to re-key the house. 

It is landlord-friendly, and specific pockets have gone upwards of 2-4x in the last 5-10 years.

  - If I understand that correctly, then I wonder if the increase value offsets the cost paid out to split the parcels up.One last thought would  whether there are any underlying benefits to keeping it as one parcel, such as city regulations, etc.- I had a conversation once in my owner's rep day job about new construction of a commercial building on its own parcel adjacent to another parcel owned by the same owner. 

Creating these entities have costs especially the S-Corp so only do what works for your specific situation.