Ordinances are constantly change, every area/zone can be different and the legal speak can be tough to crack.I have started calling and talking to them before I proceed with a STR purchase.

How tough and hard headed are you.  

I just sold one in the Historic district close to downtown and the investors is putting ADU in Basement building a garage with ADU above then on the side lot another ADU.. and that house was basically a tear down I sold for 700k.. so to make the math work he is going to be in this 1.2 at least and now you have the main house an adu above garage an Adu in basement and the other adu.. so rents will all be well over 2k per door to make that work.. so affordable  Na  planners and city fathers puff their chest out about how great they are doing proving additional housing  YA..  

My main fear was, how do i prove to the bank to let me take that mortgage on myself/company.

Even in the current hot market where appreciation is skyrocketing, this would be tough to achieve.The best strategy would be to purchase property that you can force equity into.

Always tough to 'buy-right' in your backyard, you did it 2000+ miles away!!

It's freakin tough in the market today, but still a lot of success stories out there, and totally doable if the right actions are taken.My suggestion for you would be to call some investors and agents in the Grinnell area and pick their brains on who is in the market and what is a deal and what isn't a deal.

I will be somewhat tough if you don't buy soon as the holiday bookings will make it difficult to transition, get inspections and closing dates to coincide with very tight windows and also the possibility of cancelling existing reservations for people that have big holiday bookings.Depending on what type of property you are looking at will make big difference also.

I will say that it's very competitive just like anywhere else right now, so it's been tough to find deals that truly cash flow (after PITI, CapEx, Maintenance, etc).

These are the questions you need answers to to prove they are legit buyers.