Getting that first property is exciting—and yeah, NYC is no joke when it comes to price of entry.Honestly, a lot of people I’ve talked to in your shoes end up finding better opportunities just outside the city.

You could leverage your experience while they can bring the capital. 

I’m especially interested in learning from those with experience in more expensive housing markets and from people who used really estate as a way to invest for their kids' colleges.

In Berlin, rental arbitrage has been very profitable, with average annual margins of 25-40% after all costs but before taxes, so shifting to a market where arbitrage is barely breaking even is definitely a reality check.Given your experience, would you say the best way to enter the market now is through purchasing properties with financing?

We have renters there now and they cover the mortgage with a bit of cash flow ($100/month), but the property is going to need some more major updates (windows, roof, HVAC, siding) within the next 5 years as they are starting to be at the end of their useful lives.We would like to pay off our primary residence as quickly as possible to “free us” from mortgage payments on our primary residence.My questions are below:1.

Quote from @Joel Bechtel: The agent I spoke with has about 30 years of insurance experience, so I’d hope she knows what she’s talking about and what she’s offering.I have another policy with Allstate for my 6-unit property, which they were able to insure for approximately $890K because the replacement cost came in under $1M.

I ended up making a profit that paid for my wedding and honeymoon!

For example over the last four to five years a lot of people went out and bought STRs thinking it was going to be a great investment only to find out that the numbers did not work a year later and needed to try to use it as a LTR to make ends meet. 

I'm about to sign up for a security system for my property in Philadelphia, and I was curious how Vivint ended up working for you.

As you indicated yourself, it's mostly throwing away money because you have nothing left at the end of the lease.