Quote from @Paul Lucenti: Would you rather have monthly cash flow or would you prefer a quick pay day after 3-6 months?

I am not yet familiar with the management fees for an STR yet as we self manage, however Cleveland itself is currently STR friendly and just requires them to be registered if you have stays over 90 days and then you register with the city and pay $35.

My profile has my YouTube channel and I have an episode that shows you exactly how to create the comp set and look at amenities that matter, what others are paying for cleaning and how other listings look - that way you can see how to best market your property. 

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.

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.

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.

Push through it, you may even need to have a second, consistent paying job and thats OK, until you get established.

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

Keep in mind that all this time we were living with my parents paying them rent but saving/starving to score our next deal. 

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