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.

Namely, that if a tenant (in this case accompanied by a whole family) ends up stop paying rent and I would be on the hook for both covering the mortgage and dealing with open ended legal costs and time.

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.

Is it worth to pay that much for 1:1 coaching for 6 months and a laid-out course? 

Our tenants pay $2,700 in rent and the mortgage+fees comes out to $2,360.

In fact I can have half of the rooms occupied and still pay the mortgage. 

After I make those payments then my lease with them is for $5,250 for 12 months where they pay all of the utilities.

I’ve had people who signed up for 6 months and stayed 5+ years, paying increasing rental rates.

Plus, it integrates seamlessly with accounting tools like QuickBooks, making bookkeeping much more straightforward.Whichever account you choose, look for one with no monthly fees, online banking, and features like automatic bill pay.

The struggle comes when you plan to sell, pay close attention to how the bank would treat the loan in the event you would sell.Even though its a bit more work, banks are typically open to these loans as it provides them with additional collateral in the event of default.