Make sure you talk to your tax professional. 

The advice I would give is to find some wholesalers to source deals for you, source your own deals via direct mail or phone calls, and also work with your agent on identifying deals and crunching the numbers to make sure they really work before writing any offers or contacting the seller to see if an offer can be made at whatever price you are thinking of offering.You and your agent should be a team and should be working together on doing what's best for both of you.

I don't want to stutter and stumble on the phone with a realtor because I can't answer her questions.

The investors that claim to be "killing it" with their vacation rentals are usually slaves to the phone, doing all their own cleaning and maintenance, etc.

Smaller properties are more stable in that people stay longer (traveling professionals is who you should be marketing to), they are less seasonal and maintain rates year-round, and even if they do get trashed or something gets stolen its a lot smaller recovery cost.

These are professionals with additional training and a stricter code of ethics.

The biggest point to understand is that you can build a professional team in any city. 

There is no shortage of professionals here that have been exactly where you are.

If you are the prime and pulling the permit you need GLI and possibly workers comp and possibly professional liability.

Please leave your full name, cell phone number, and the property address and I will call you back as soon as I can.