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.

No, your nobody special and do not garner any "relationship building" or any of that jazz UNTIL or unless you make yourself special to them to garner a volume relationship. 

Or, should I focus on just holding these forever type deal and build a cashflow monster? 

Still can be very beneficial for a new investor but personally I think not as good as a service as they had with their exclusive listings where they had inspections already done, rent rolls available, and you can complete the entire offer/acceptance via their platform rather than being handed off to an agent. 

You should reach out to @Melissa Haworth she can get the actual numbers/rents on STRs in the area to help run your comps.Each building is different, each area is different, it is important to find accurate data to make good decisions.

With thoughtful planning, you’ll be well on your way to building wealth and achieving your goals.Good luck! 

I had been discussing this property with the owner for a while and saw its potential—distressed but with strong fundamentals and built-in equity.The deal was a great opportunity to apply creative financing, secure a property with minimal upfront capital, and build long-term cash flow.

Let's break it down with precision:The "Pain" (At First Glance):Your $2.8M sale splits out as:Building (§1250): $2.3MPersonal Property (§1245): $500KOriginal Basis Allocation:Building: $1.6M (depreciated over 27.5 years)Personal Property: $400K (fully depreciated)Building Depreciation:Annual: $1.6M ÷ 27.5 = $58,182Total over 10 years: $581,820Gain Breakdown:Building (§1250):Sale Price: $2,300,000Original Basis: $1,600,000Less Depreciation: ($581,820)Adjusted Basis: $1,018,180Total Gain: $1,281,820Unrecaptured §1250: $581,820 (25% max rate)Capital Gain: $700,000 (20% max rate)Personal Property (§1245):Sale Price: $500,000Adjusted Basis: $0Ordinary Income: $500,000The Strategic Play:Remember those suspended passive losses you couldn't use?

@Emily Pena building houseboat community in anticipation of rising sea levels?

I've had pretty good success the last couple years with a combination of house hacking and building Accessory Dwelling Units.