New in Yorktown Heights, NY (Westchester county)

[John Merryman]

Greetings everyone, I'm new to the site and to real estate investing. I'm 39 and live in Yorktown Heights, NY where I own a house with an accessory cottage which I rent out. I guess you can say I'm house hacking. My "day job" is running tech (mostly software dev) for an internet startup, but I'm realizing that I'm not a city guy and all of the demand for my tech leadership skills force me to be in New York City. I'm lucky to have made some good money at my last startup, so I'm hoping to parlay that into a real estate business and avoid the city lifestyle.

When I'm not working, I enjoy riding my horse, flying planes and working on my house. My profile pic is me riding in the Bedford Riding Lanes hunter pace last month. I love doing DIY projects, especially home automation. This past weekend I installed additional wifi and instrumented my pool to monitor and log the temperature over the internet.

I've got two questions for everyone

1. I live in a high-cost area where multi-family homes needing reno list on the MLS for 200k+ even in marginal neighborhoods. Single-family homes are even more pricey. Should I start looking further from home, explore foreclosure/short-sales, or just try find some cash flow locally even if it's well below the 2% rule?

2. If I want to put properties into LLCs for asset protection, any tips on how to get financing? I want to avoid having my assets at risk. 

Thanks everyone!