I am wondering however if I should transfer the asset to my new LLC and then apply for a HELOC to get a head start on building business credit.

I've found its pretty hard for folks to get comfortable with a purchase out of state if they haven't seen the general areas that they think they'd like to buy in.While I love where your heads at - best thing you can do right now is likely focusing on saving cash, REI education, paying off loans, and enjoying your last year of school!

My rule of thumb when it comes to this is get someone out there (3-4 contractors) and get them to bid the job then the more you do that you can quote off the top of your head when you see a project.

But your heading says STR Insurance, and I don't know if the number of STRs will decrease by a huge amount because people will still vacation there. 

Hey There @Scott Bogue - First just a heads up - YOU ARE NOT ALONE & YOU WILL PERCEIVER!

As for use as "finished space", a basement can add SOME value but typically the head height may be lower, it doesn't have large windows etc.

While the other would always have strong rent potential potentially reaching into the $3k if it is heading toward CA prices, seeing how Californians are moving here in herds.

So part of the 40k pays for that service and over head. 

It’s so over my head now what they are asking me to do that probably won’t make a difference anyways.

That drive will do you well heading into your future.