Perhaps emptying it so that it can attract an owner occupied buyer is a good alternative or hiring a PM company to off load some of the work there for you.

It would be much easier and safer for you to do it yourself.

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. 

Probably because she is yet again being marketed as the alternative to D.T. and that's it, no reason FOR her just go for K.H. because she's not D.T.. 

Lastly if any dangers, from ADT Crime map I found San Antonio to be a bit more safer than Dallas and Houston. 

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. 

My other alternative would be to save several years for a down payment.