3️⃣ Local Regulations: Before you invest in a short-term rental, it's essential to understand the local rules and licensing requirements.

I understand I likely won't have an HSA debit card like I do now, and that it would be harder to liquidate my investments potentially.

I believe you mis-understand the process.

Understanding that you're in New York and the laws are leaned to be tenant friendly, I would still say this is the best way to go about it as a new investor.

We've never actually had a tenant use it after reading the addendum (which was our goal), and I think it helps prevent problems when they understand the myriad issues involved in its use.  

My understanding is that the market is more important than the property.

As far as the sale of a property with a mortgage on it, that all gets sorted out at close. ie, you bring your money, the bank gets what they have coming, the realtor gets what they have coming (if there's one involved) and the seller gets the rest.

So you can understand why I was blown away to see prices half that or less with rents 1500-1800 in Duluth.

- You or the PMC can get 3 bids, but who is going to know how to accurately compare them and understand if something is missing - that will require more work+charges once the project has started (a standard tactic by many contractors!)?

Quote from @Zach Rothman: Sorry guys, I didn't really understand what this is about.