Once the work was complete, I refinanced to pay off the hard money loan and held the property as a long-term asset.This duplex also marked the start of my short-term rental journey—we ran our first Airbnb from one of the apartments before scaling to bigger projects.

Hey @Keagan Scott, so I don't have any insight into Gary, IN but here is a blurb -"Those looking to rent out their properties for less than 30 days (about 4 and a half weeks) will have to get a permit, pay a one-time $150 fee, and have a city business license.

The tenant fails to pay their last month's rent and leaves the place needing new flooring and paint.

If your situation hasn't changed much, it might not be worth paying more for premier.

So, you can do a land contract for 12 months, which should allow lender to credit you full value of the land vs the purchase price, but the loan will pay off the land contract, so the lender maintains first lien position.Can't help you with the rest of your question, but you should be able to search for "CPA" here on BP to find experts to reach out to.

One would think that a bidder would pay $45,000 in my example (since they are assuming the first mortgage), but they are actually bidding $225,000.

Note both of these options require paying the tenant to vacate for a no-fault eviction (terrible name as if lease is up it is not an eviction).Note terminating a lease agreement for the purpose of rehabbing the unit is under attack in some places in the county. 

The commissioner ordered me to pay the plaintiff over $9k plus her attorney fees.

You might not cash flow right away, but even just offsetting what you were paying in rent while building equity, getting tax benefits, and learning how to be a landlord is a game changer.

It looks good) I stumbled across someone locally who does it, but I'm sure you could find someone there if you or other out-of-town investors like the idea of paying a bit more for that level of security and obtain a remote monitoring source of the exterior of the properties.