This is where expert mortgage brokers come in, acting as your guide through the maze of real estate financing.

However, on my back burner is a direct booking site and I'm leaning toward OwnerRez (once I get through Ski Season).

I recommend you read some books on how to manage investments well.

My recommendation would be to engage an investment property focused realtor (not a general residential realtor) and let that person guide you through the process from pre-qualification to market/property valuation and selection. 

Saturation is definitely upon us but quality product continues to get booked just like other markets.

Thanks for the advice, I have read some books but not that one.

The Long Distance Real Estate Investing book by Bigger Pockets is gold!

Transcribing transactions from bank statements, posting transactions to the correct accounts, and then manually creating an income statement, statement of owner's equity and a balance sheet is a fairly time consuming process and I have not been able to keep up with the book keeping between my regular work responsibilities.What accounting software do people recommend? 

Would love to add a mentor to guide us through the first deal, we can offer all of the sweat equity and our network that will help fundraise the deal! 

Less bank accounts results in less check books, less debit card numbers, less account numbers that you have to track.best of luck.