.• Clear Guidelines & Performance Metrics:Defining clear expectations, call scripts, and performance benchmarks helps maintain consistency.

I don't know how long you have owned it but I am willing to bet if you have owned it for at least a few years you probably have a rate on that property that will be hard to get again. 

Your best bet are the (relatively speaking) higher cash flow markets in the midwest and southeast and perhaps a few in the rust belt.

I should note that this may be considered manufactured spending To your last point of the gifts funds....Per Fannie and Freddie guidelines, lenders can't allow gift funds on investment properties.

I am betting they would be rather rapidly absorbed. 

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!

I suspect a local bank or credit union might be your best bet.

Quote from @Anil Shah:  Short answer - if they originate a loan that they want to sell to Fannie Mae and Freddie Mac, they need to follow their guidelines.

That’s the best bet.

I bet there is if you ask around.