The concern he had and to be fair he said he needed to research it (i am just doing some of my own) was that since most of the work and hours will be conducted in LLC now and the LLC does not own the property would that create any issues with my ability to file a schedule C and claim depreciation and losses, etc?  

It would be much more expensive for me to turn the water off and on than to just have a bill for $40 for three months.

I have built a lot of websites in prior careers but what you will need is a way to show the availability calendar to sync with all your other platforms and the ability to take direct transactions through Stripe or Square. 

House hacking gives you the ability to learn firsthand what it's like to be a landlord, offset your mortgage using the other unit and to reap some tax benefits.

Context: My dad has assorted health issues that limit his physical abilities and does not want to fill out forms or devote much time beyond discussing things with a Lead, reading over anything he’s signing, and sending a check.

My agent says the only way for her to get back the ability to write me Hartford insurance, was to send a written notice that she was to be my agent with Hartford. 

If you bought 5 properties with $300,0000, they all need to be throwing off a total combine of 20% return to get that $5,000 (as the example above shows), to get that expense coverage for your ability to leave your job. 

I would then want to know if there are any access easements to the rail line or restrictive covenants on the property which would negatively impact my ability to develop the land.Lastly, my concern would be environmental.

That'll give you around $420/mo instead of the $650/mo in savings, but:- You'll have liquidity in case you find something better to do with the money- You'll have the ability to refinance at a potentially lower rate in the future as @John Mason points out.- You won't extend the term back to 30 years (which is definitely part of your monthly projected savings). 

So while the technology may be running quickly, the ability to warehouse it and let it really conquer America are well behind the curve.