If the condition of the units is in great shape and well-updated then I'm sure it's well justified to bump the rents up.

you could find yourself underwater pretty quickly and consistently if they are not in pristine condition. 

For now, simply increase your homeowner's insurance liability coverage to $500k-1M and get a $1-2M umbrella policy (costs about $200-400/year), which provides better protection than an LLC for house hacking situations.Local Volusia County Concerns: Property taxes in Volusia County average 1.1-1.3% of assessed value, and without homestead exemption on the entire property your taxes could be higher than expected—confirm the exact annual tax amount and whether homestead will apply.

When tenant leaves, they need to pay to revert the premises back to its original condition.

Look at their condition. 

So, I will never be able to tell buyer what exactly it will cost them to fix the property.

Hey @Brice Peterson, this is exactly what I do and I am up to four investment properties so far!

The key is to get everything in writing — a simple agreement stating that you’ll pay them a set amount once they’ve fully vacated, turned in the keys, and left the property in acceptable condition.

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@Tajana Reagan in general when doing high LTV loans the largest thing that seems to come up in my experience is appraisal issues, not always with the value but often with the condition.