We also have homestead exemptions where I'm at - which an LLC isn't able to take advantage of - so I would investigate the benefits of that as well when considering selling it to yourself.  

And you get the benefit of having over 100 past ones to catch up on.Locate and attend 3 different local REIA club meetings great place to meet people gather resources and info.

The listing is currently visible as ready to be in service, and I've already received three bookings.My question is, will I still qualify for the short-term rental tax benefits or loopholes if I have blocked off dates until September 19th due to these repairs?

From what you said it sounds like a short term rental could be a good move, and the tax benefits could be significant if you look into the short term rental tax loophole. 

It will familiarize you with the basic terminology and benefits.

The main benefits are doing ceilings and if you needed to paint a bunch of doors.

Maybe commit the refinance funds to buying another property at a much rate of return than the loan and your partner will see the benefit in refinancing? 

Free market is good when some chosen/special folk benefit from it.

Regarding single member vs. multi-member LLC's, you need "Charging Order Protection" (COP) to receive the best asset protection benefits.

I wonder if there is any reason why the business can’t do it at discount given it’s a new business and take losses to build the experience benefiting ME as the owner of the lot.