But then again, no one ever went broke paying tax on profit. 

I did a search on the forums and insurance seems like it could be a major problem.Shouldn't be an issue at all. 

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.

One of the above houses was a foreclosure, now bank owned and on the MLS. 

I would check the rules in all of your jurisdictions.

As such, I keep them in one account and just track any deductions with a spreadsheet for each tenant. 

We do lending and we ask the question - if you have been doing this for ten years and don't have any money where did it all go? 

Would love to connect, regardless of real estate experience I know we could all be of value to one another.  

Quote from @Tove Fox: I live in California and am interested in purchasing my first investment property in an A or B neighborhood in one of the above states, ideally under $300k.

Try this one: Birdsong v.