Any update on this @James Celidonio

Weirdly, you may actually be able to get better terms and/or more LTV on the refinance if there is debt on the property as lenders have rules for max cash in hand (max proceeds you get at closing) for cash-out refinances.  

Just wondering can you ever catch a great deal on the market  and if so what’s stopping you from taking advantage?

I've separated out electricity but not water (never heard of sewer being separated) and I've always had separate gas meters on my properties but have separated the heating system on one.

At the bare minimum, you should do the following to make your bookkeeping easier:Dedicate one checking account and credit card exclusively to real estate.

I have an STR and previously did not allow pets on our property out of fear that they would destroy it. 

Hey @Erika Andersen I totally hear you in wanting to save some money and taking on the task yourself.

You rent it for one year and create a successful STR business that shows a trailing 12 month net income of $75,000.  

What do you do when in house goes on vacation? 

I would add to this one pound into you the good relationships you have with the contractors and agents in your area will be your best and most helpful relationships.