My partner's family owns an STR, free and clear, worth between 1.8-2 million in a popular vacation destination.

Figure out what it’s costing you a day and start there. 2) Increase pet limit to 50lbs. 10lbs is an extremely small pet.

They claim that the replacement cost has gone up 400k since the policy was written, and that they had just raised rates this past January.  

I dollar cost average, more or less, with this too. 

Often times, I will do that for free especially if I'm going to be nearby, but if they do it more than once in a short period, I will charge a fee and they aren't surprised by that either.

@Steele KruzelThe $60k should go towards your cost basis. 

I work full-time as a CPA audit manager at a Big 4 public accounting firm, and in my free time I would love to help and learn from an experienced investor with strategies similar to what I’m interested in (appreciation, single family (potential multi family), mid-term rental (potential short-term)).Open to any advice as well on how to make my first leap into actual investing!

The annual insurance cost of $300 is way too low, I'd add another 0 to that.

His rehab costs were less than what I Typically pay to paint the interior of one of my rehabs.  

Most people assume house hacking means you have to live for free but that isn't true at all.