Rents will probably start to go up in 2025/2026 when we burn off some of the new build multi-units, but rent/price ratio is not great today. 

Any company insuring your properties without an inspection most likely has a clause buried deep in their policy allowing them to deny claims for conditions found on the property that do not meet their UW standards and they will deny you claim based on "the house should have not been insured with them anyway".Although the inspections can be annoying look at it from the other side.You pay them 1000 to 3000 a year to insure a rental property where they agree to pay out possibly hundreds of thousands of dollars if it burns down or up to 1 million if a tenant slips on a bananna peel and falls down the steps or the tenants dog bites someone and since you didn't enforce the tenant having their own renters policy to cover the dog bite the landlord's policy is paying out.The insurance company is very much like your rich uncle backing your business venture - you run the business, he takes on the financial risk from disasters, and doesn't even get a say in who lives in the property.Your rich uncle asking you to fix the steps, put up a handrail, etc which is in your and his best interest long term.Do you really want to rent out a property with a busted front step and a bad roof that is going to leak sooner than later?

I am a big believer in investing for appreciation (especially if it was forced appreciation), but $800 a month negative is just too much to swallow IMO unless that property was appreciating well over that every month and you had endless cash to burn.

I work a lot in this space, and I've seen too many people get burned relying on someone else's numbers. 

We have a newly renovated property in Baltimore that has been empty for a few months because we lack a PM.  (This is an out of state property for us)
Last year, we connected with a property manager through these foru...

Sounds like there are several unhappy customers of Neal Aviation (Garrett Neal is the owner of the company on record) for being sold bad parts and they're burning suppliers with hot checks for parts for privately owned aircraft (in their more recent business reviews).

I had a client get burned because of this and it made things awkward. 

However, text message marketing requires adhering to specific guidelines and best practices to remain compliant and avoid facing SPAM complaints and/or potential lawsuits.Those who do not comply with the strict SMS guidelines and regulations can not only face angry customers, suspension from messaging platforms, and unwanted legal action.

Would love to hear from either of you, @Hayden Burns or @Matt Burgess about how you've navigated this.

I wouldn't touch the <100k properties...if you're looking to build long-term wealth.There's a good chance they will burn you.