Seeking stable, long-term housing can lead to longer tenancies and lower turnover costs, which is what many Section 8 renters are after.There are, however, disadvantages to take into account.

You and your cleaner should form a type of business relationship that will last long-term, which benefits the both of you.

I’m wanting to know there are specific things I should add into the contract before beginning the work, ie: terms, payments, timeline, etc.

@Trey Onufrii It's tough to say which one is the better investment without more details, like - cost of each parcel(s), are there utilities close by (especially the Jomax site), what's the terrain like on the hilltops? 

I currently have 2 long term rentals, looking to add more cashflows.

Check out this link for more details on QuickBooks Online.Gita Faust

I am planning to start a direct booking site for my short-term rentals.

The combination is that high LTV financed RE is not only at an all time high but in terms of inflation adjusted cost is at greater than 40 year high.  

In terms of advice, it seems like you have a solid plan of what you're looking for so I'm not sure what else I can add other than I think it's a great idea.

I'm looking to do a house hack and open to doing STR, mid-term or long-term rentals.