They work directly with agents and should have a good sense of which areas in town are "most popular" for placing residents and which aren't.

But, isn't Yale University more popular since its one of the Ivy League?

While chatting with their team is fascinating, there is an absence of online information available about the company, the team member told me neither him nor the director have LinkedIn accounts and no alternative was provided to review their achievements or qualifications. 

Might be able to get a contract with the buyer of the cherries and thow some cash at you upfront for signing a agreement to buy the crop but I don't know what the alternate bearing looks like on Cherries in Washington and the brokers may not be willing to pay upfront in that area... or a upfront lease payment from the renter... 

Given that it's almost a 50% increase from the existing rent price, you might want to set a timeline of 2 or 3 months before it taking effect so they can find alternative housing if they plan on vacating instead of staying at that price point.Another option could be to ask for the rent increase, but offer something in return.

Any advice or alternative routes I can do to move forward without having to start from 0 somewhere else is extremely appreciated. 

The alternative is to just pay your mom's rent and let another owner deal with your siblings. 

Oregon is also an increasingly popular retirement destination, for primary and second home buyers that don't need to have STR permissions, the options and areas to invest are robust, and there is even high demand for upgraded and updated furnished mid term rentals to help off set operating costs.

Here are a few popular options for inventory management in the STR industry:Smartbnb: Smartbnb offers tools for automating messages to guests, but also includes inventory tracking features.

Alternatively, if its for the hopes of accessing future real estate loans via the LLC then it may be a moot point as a lot of these bigger banks won't lend on an LLC that's brand new and no history of cash inflows/outflows.