Insurance agent in Atoka, OK and insuring properties in the area regularly. 

Or just clean up the loans to get them into a single loan?

The wholetail is a smart play, but you should be cleaning the place thoroughly and doing no repairs and then presenting an honest proforma with rents and expenses estimated so investors have a PDF to look through.

That's 73 turnovers and at $200 per cleaning, we're at $14,600 for the year. $400 a month for utilities, $500 for misc expenses like toiletries, maintenance/repairs, landscaping etc. $150 a month for insurance (this might be low?).

We are concerned that the smoking/smell will turn off prospects as well as the extra cost of cleaning up areas after smokers move out.The building is in Illinois. 

Pretty much a regular Florida weather breakdown.

Lastly, try to regularly assess and adjust your goals as your financial situation and priorities evolve, which will help keep things balanced and flexible.Keep learning and growing!

I haven't responded and prefer they send a regular mail letter to my PO BOX.

I have used two companies, and while they are both more expensive than regular insurance, they have extra coverage that is specific to STRs.  

Based on all the facts and circumstances, you participated in the activity on a regular, continuous, and substantial basis during the year.