Hi Robin, nice to meet you on here. I am not as active on here as many other contributors, but your post caught my eye as I am in a similar boat as you.
My wife and I live in NYC, make good money and we are closing on our first single family investment property on Cape Cod (MA) in a couple of weeks. We will be renting it out primarily as a weekly summer rental and weekend rental in the "off season" where we aim to net $400-$500/month positive cash flow.
We bought this property off market through a friend of a friend who was going through a divorce. We acquired it just under market, but we considered this a heck of a deal because it was turnkey and it is located in a very highly desired neighborhood (Cotuit) where weekly rentals in the peak season (June-August) command upwards of $2,000-$2,500 per week for our type of property.
In terms of financing, we have a family friend on the Cape who was able to approve us in about an hour with our strong income and credit history. We financed 80% of the purchase price with a 10 year ARM at 3.3%. I definitely recommend you leverage your income and credit history (if it's clean of course) to increase your cash on cash returns if your risk tolerance is at a place that allows such leverage.
Good luck and let me know how things go for you.