If that is not possible, you understand and will allow them to break the lease early with no penalty. 

I'm absolutely clueless, and am looking for anyone who is willing to share their experiences, advice, or point me towards resources that could help in understanding the market better.

Thank you for your kind words and understanding.

Ryan,Here’s how you can handle the situation with your tenant who is $150 short on rent:Check the Lease: Look at your lease agreement for rules about late payments and fees.Communicate: Remind your tenant in writing about the missing $150 and any late fees that might apply.Stay Firm: While it's good to be understanding, don’t accept partial payments going forward.

VRBO doesn't seem to understand what we are requesting. 

The hot tub can be a pain so understand a certain charge but $1800?

Once you experience and understand the business better you can always flip down the road.

As a beginner, I understand running the numbers as far as rent comparables, but also know there's more to consider than that. 

Both moved in back in 1970s, so they are probably in their 70s of age now...Now, I understand that these tenants are "untouchable" in San Francisco, and your only hope is to wait until their pass (sorry to say that)..

Need a referral for a solid escrow attorney who has experience with subject to deals.