Secure the unit for the dog and your tenants safety - meaning all doors and windows should be functional.

Hopefully Madison, WI will take note and ease up on some of their anti short term rental ordinances. 

No on-site office, nearly autonomous functionality.

Tenants don't see any difference between a den and a bedroom as long as it's a functional living space, so you won't run into any issues thereIt's unlikely that you would have to pump out the system more than normal with standard usage, but one thing I would recommend is to always ensure your septic alarm is fully operational.

No on-site office, nearly autonomous functionality.

Renters, ESPECIALLY those who know they are only looking to rent for a finite period are generally focused on function over aesthetics.

I'd prefer the bulkhead as it has more functionality, but not sure if that would satisfy code to make it a "legal" bedroom.I am hoping to refinance the property after I make the improvements to get my money back out, but that would definitely require the additional bed and bath to meet code and be considered legal.If anyone has the answers here, could point me in the right direction of where to find them, or just has any advice in general, I'd really appreciate the help!

This is essentially a $6,000+ job of a brand new panel and outside shut off valve for what was previously a perfectly functioning system that had never given any issues. 

Prospective renters will let you know if the property is priced too high, needs work, or the property has some functional issues that's keeping them from submitting applications.

Either adding square footage to an existing functionally obsolete 2/1 or 3/1 or splitting off a double lot.