Have you established your overall goals yet?

Tenants trust us too, but theres a lot to be careful about.  

The building has been passed over by many people due to the layout, but I have a creative and viable solution (boutique hostel/hotel hybrid in well-established and overpriced tourist destination). 

At this point, they establish the total town budget.  

You can earn honorable discounts and fees overtime by establishing mutually beneficial partnerships with one lender or broker but squeezing them dry for a lot of hard work and not equal pay isn't something I recommend making a strategy

I'm not advocating he establish a new LLC without using an attorney or registered agent to define the bylaws of the agreement.

In your proposed situation, here is what I would do:1) Make sure you have a good/solid/reliable contractor that can actually do the work and has capacity to handle the project.2) Apply for the max HELOC and get it established. 

The superb amenity offerings and number of charming listings in the community have led to an established brand vacationers and guests trust.

There is a lot to be translated from general professional experiences to real estate, including finding great people.

Anyways, I appreciate all the feedback, it's given me a lot to consider.