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.

In either instance, I would certainly have an attorney make sure everything is buttoned up and legal to protect you both.  

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.

That's not a normal experience.Dating apps are the "easy button" for relationships.

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. 

The way I know is; I send the company a list of my customers and when I get the list back the email addresses and phone numbers are accurate.SInce, it sounds like you have not used this type of service before, I will tell you what to expect for and and every other service provider.If you send any company a list of property owners that you own and you want the company to give you the phone numbers and email addresses this is what you can expect .Send the company 3,000 property addresses - you will receive about 1,000 phone number and 850 email addresses.

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

Depending upon the local laws, it may be possible that any similar property could be a STR just by a few clicks of buttons to post it online.  

@Owen Fogarty I just give my customers a Google Sheet template to do the accounting for flip income and expenses.