Michael,I have a lot of customers that live in California, Texas, Florida that have been buying in both Indiana and Ohio over the last 3 years.

Ideally I'd like to buy the property, build another house in the large back yard which has access to a neighboring street for a driveway (also not sure if that would be allowed), and then sell that house completely separately.

After finally getting into Hostaway, I felt it wasn't for me and the customer service was not very prompt or helpful with the issues.

You can also get a acquisition line of credit as we have done for one of our customers/partners.

Here is what I was told or found out by some of the suggested companies.Safely- Told that they are only accepting new customers who have 20+ short term rentals at this time. 

They gave you two options that both work out great for them and are not ideal for you because they are a bank.

This is the stage of the process where your lender can issue your loan docs out to escrow/title/settlement and these folks can schedule your signing for closing.Before it can reach CTC you'll need to make sure all income/assets/credit remain the same so that means no changes to your credit that are bad or adverse, no job or income changes ideally, and hopefully those funds you've set aside to close with are still "there," so we can keep this closing on track.If you had any questions left feel free to fire them off.

You should be able to customize this with your manager and adjust over time. 

You can set up templates to save time and customize them to match your brand.

This does require owner occupancy of both units for at least a year for condo application submission, but also assumes a number of other things including that nothing was performed with respect to prior historical tenancies that would disqualify you from a condo conversion.While the aforementioned would be ideal, it would be all for naught if Planning determines that if at any one time the ground floor was rented in the past.