@Kyle KipkaI strongly disagree with the suggestion to create a separate column for overhead expenses.

I worked really close with my insurance broker this year to make sure all of our properties were properly insured too because of rate increases and he assured me that my primary covers it and it’s listed on my primary and it’s also listed on the separate umbrella policy.  

We aren't using the garage at all and aren't planning on doing so, so we thought on making it a living space separated from the house for rent, which we'll sacrifice 1 of the bathrooms to add it to it, and later on do the same with 1 of the rooms as well, though I would have to make an extension to add the rest (kitchen, bathroom, etc.) so that way we could take advantage of the space we aren't using. 

I have a separate computer set up for QB that I don't use for personal stuff.

Purchase price: $250,000 Cash invested: $40,000 Took a three bedroom ranch home and converted into two separate apartments with two tenants.

I will DM each of you separately. 

Hey @Atlas Blake, so the catamaran idea seems kinda separate deal to owning a STR.Is the plan to maybe buy or build up a small resort type place and do the catamaran thing as part of the stay?

If I'm following this correctly, the 1st issue I see is that you have an "active" business (consulting) versus a "passive" business (the rental property, assuming you don't do hands on management, etc.)...this would be a separating line for many people I've talked to about this. 

Add in things about yourself to separate yourself from the big buy companies.

Separately, I use apartments.com to collect rent, security deposits, bills, etc - also free for you as the landlord and the tenant.Third - to write off items for taxes, I'd check with your CPA but in general, it would be anything you spend money on with that property, including mileage going there.Best of luck!