Once you have a few more properties under your belt the transition to full time real estate may be smoother.  

Coaching and mentorship will definitely save you huge on coslty mistakes as well as help you fast track your transition and scale the business. 

Also after that how hard would it be to transition more into the BRRRR method.

Once I educated the LA  everything went smoothly. 

Its good to have someone that can make sure your first couple deals go smoothly.

Most rent-by-room tenants are in a transitional phase in life, and will be willing to pay a premium for a clean, safe, respectful environment.

This one was relatively smooth and had no surprises behind the walls, which is always a huge plus!

The process working with them was pretty smooth.

On a JV you may make less as will have to share the profit , but you rely more on a capital partner for the funds as well as share the risk if the deal is not as smooth as anticipated.

This property being purchased is very old (130+ years) , and its understood that this thing will need a lot of repairs in its first year of new ownership to maintin this thing..The biggest question is after setting up the above scenario with a Land trust and LLC is A: thinking it would be more tax advantageous to claim all of these repair expenses to the LLC rather then in their own name (correct me if I'm wrong on that) B:want to learn the ropes of owning and operating an LLC, seperating all bank accounts, for future growth of not only aquiring more rental real estate but also possibly transitioning to full time running the LLC as well as starting others (a transition away from my 9-5 as a way to have a more flexible schedule for my children and family) .Is this a possibility or is the entire idea of operating an LLC which is create off an asset owned in and trust not possible?