Currently I own a large real estate company and still get some great value out being in his inner circle of real estate operators. 

Hi Jon from Boyertown, PA-You and your fiancé are interested in buying your first short-term rental and wonder profitable areas to purchase with a budget up to $500,000.I would look at places along the west coast of Michigan, Grand Rapids, Kalamazoo, and near Ann Arbor, MI.It is important to understand the local STR regulations in each community and partner with a property management company that can help your navigate that and manage it well for an excellent guest experience.Don't forget to look into bonus depreciation and doing a cost segregation study to increase the tax benefits of ownership and if you "materially participate" in the management of the property per IRS guidelines it can offset active W-2 income which most real estate cannot.To Your Success!

The company wanted me to push stocks and bonds, but didn't want me recommending anything they didn't make money on.

A good attorney, RMLO, and servicing company play a big part of this. .

Trusting what the franchise tells you is foolish.I can tell you this: there are companies selling leads to real estate agents all the time.

VA company?

Best of luck with your property management company!

I would definitely look into seeing if there are any AirBNB arbitrage companies operating in the area that may be willing to take it on. 

I do all accounting for properties and company in Rent Manager. 

Any PM software should be able to do everything you mentioned.I am not a PM but I am an Accountant/CFO for PM companies and real estate investors.