Understand the demand for short-term rentals there, the peak seasons, and what similar properties are charging.I would also suggest networking with others who are already investing in that area.

My plan is to monitor those rental listings during the fall and winter seasons, and see which units are more consistently booked.

I truly appreciate the advice and experiences shared by seasoned investors here and look forward to learning from your insights.

Add to this its very seasonal, most places struggle to get any occupancy during the winter.If you want to discuss the Virginia Beach Norfolk area shoot me a message, there some opportunities here.

From what iv noticed, the big time players who own hundreds of doors typically own their own PM company.

Hello Cory, thank you for your input, I appreciate this from a seasoned investor and one who has boots on the ground.

Seasonal. 

Please provide useful advice on locating, assessing, and negotiating private money lending deals, especially from seasoned professionals.

Interesting, I was reading the Key Data report on Next Season's US Rental Trends and noticed they include owner nights and hold nights in their calculation.  

The devious and unethical players can rip you to shreds in the commercial space if you do not know what you are doing or do not have good representation.