Is either one of these options feasible and how can I ensure a win-win for this 70 year old seller and for myself and any other financer?  

It's better to deal with a reputable larger firm vs. mom and pop shop to ensure they are doing everything on the up and up and someone isn't going to lay claim to your property in 3 months from now (like a divorced spouse...I've seen it happen)People's opinions are going to vary on the hard money. 

However, I would hire an attorney anyway to ensure it gets done correctly, and it adds only $150 per filing for the attorney, all of the other court fees I would be paying anyway.Banks/lenders won't typically loan money to LLCs, unless they have assets in them that can be used to fully collateralize the loans.  

For the 1st mortg, to ensure it's not a new purchase you can also set the parameter for purchase date (set it for 3yrs ago or whatever to ensure you don't get anyone who just bought in the last year). 

I would also be curious what people recommend to improve the efficiencies of some of the expenses.... ie: brands of low flow faucets and shower heads, wifi thermostats with limits etc.... 

You're on the right track as long as your lease has been vetted with a real estate lawyer which actively practices in tenant/landlord litigation, again actively practices - very important - just ensure that is balanced, if it's too landlord friendly that's not good either but your attorney will be able to find that balance.

Scotts book that ideally you would want to show up at random times to ensure things are going as they say, but Idk how that is expected if people aren't doing this full time.

What are some things I need to make sure are covered in the deal and what should I do before had to ensure I get the best benefit? 

Ensure that we have some income while working on said projects. 2.

What should we be looking for in a CPA to ensure that we are getting the most out of having the LLC?