As far as meetups go, you can find a lot of local events posted here on BiggerPockets: https://www.biggerpockets.com/forums/521-real-estate-events-...I also have a list of Chicago meetups that I can share with you as well.

Doable if you lean on local boots-on-the-ground (realtors, PMs) and avoid another Cahokia overprice trap.

I would visit local meetups for real estate investing, and also network with agents in your area that work with a lot of investors.

I'm a local real estate broker, investor, and manager (100+ rentals, mostly Airbnb/STR and multifamily).House hacking is a tried-and-true method and in Sacramento you can produce some meaningful income while enjoying the appreciation and tax benefits of owning real estate.

*Any red flags unique to the Pittsburgh market.I’m also hoping to connect with fellow investors, agents, or property managers who are familiar with the local market.

Since you're open to markets beyond NYC, you might want to connect with local investor meetups or REI groups in those areas to build relationships with agents, wholesalers, and lenders who understand the nuances of each market.If you're looking to break out of analysis paralysis, maybe start by narrowing down one or two target markets and running numbers on actual deals.

Short answer: not legally, but they can get away with it.Long answer starts with a fundamental concept of our tax laws.

Why don't you join a local landlord association?

You might want to find local rei meetups to meet people in your market that are doing deals. 

Passive Pockets, Meta (FB/IG) ads, local meetups are good places to find groups.2.