I highly doubt I'll be able to find anything suitable in my sub $300k budget.  

I have found that ignoring one’s instincts almost always leads to problems.Keep looking for a more suitable tenant.

Therefore, I'm uncertain if my past experience will aid me in finding a suitable real estate agent for investment purposes.

Just get in touch with a local realtor who specializes in short term rentals or with on of the best short-term rental property management companies in town and they will be able to provide you with suitable properties and even give you track records of previous years so you know what to expect.

If you have a property that is suitable for a Vacation Rental, where do you advertise? 

This option is flexible and suitable for ongoing expenses or projects where the total cost is uncertain.Tax Breaks on Cash-Out RefinanceInterest Deductibility: The interest on a cash-out refinance can be tax-deductible if you use the cash for substantial home improvements.

If anyone has any referrals, experiences to share (positive or negative), or think you are a suitable tax professional yourself, please feel free to reach out to me!

Works great but you will weed through 90 people before you get a suitable applicant 

So he said he hound a property in Plainfiled IL that was suitable for a Lease to Own.

And you are correct, you always have to watch out that you are getting advice that is suitable for your particular situation.