I guess the previous owners didn't notice or care.

Let me know if you have any questions  Hey @Connor Thomas, you're learning the #1 lesson of real estate investing, which is to run your financials carefully in advance!

Condos have a lower price entry point, but many are facing insurance assessments due to rising insurance costs, so that has to be reviewed carefully, but single family homes are seeing the same rate pressure unless very new construction. 

of course all of those things help cash flow but is it realistic will it work.also your more than 300 negative as you have no money for maintenance or cap ex.the easiest way is to reduce debt. or if you think there is really good upside just pay the negative its just a small number who cares . 

I think for short stays most wont notice and those that do will not care much.

Likely your tenant is already aware of this, but I understand its a sensitive topic and a big jump as well - if they've been a good tenant so far, it could be worth it to have a convo of raising the rent but giving a discount for them taking care of XYZ on your property/ies. 

. - Not something most landlords taking care of their properties have to worry about.There are limits to clauses they allow in your lease.

However, we also learned that even in high-demand areas, careful buyer vetting is key to ensure smooth closings on fast flips.

You always have to be careful when doing business with family.

Lawn: if it's in a HOA and you care about maintaining the look of the exterior, owner should take care of lawn.