We originally planned to do leases only but pivoted to STR to maintain access to the older part of the property that will need gradual upgrades we aren’t immediately ready to fund.

PM company ruins the day-day, and I see a gradual rent growth as well.Option 2: Sell, take the gains and use as my down payment (20%) on a property in the 300K range.

As to when that will happen, I would assume it will be very gradual until all the eviction moratoriums are lifted.

Drop it gradually, maybe to $1450 or even $1400.

Thinking that we can raise it gradually but trying to think about how we buy out my aunt.

In that time, they work on: learning the property management side of the business; gradually increasing rents until they are at, near or above market rents; building their savings; building equity by making minor improvements (ADU's, adding amenities like storage and laundry, other cosmetic upgrades, etc).After that 2nd year, house-hackers look to get into their next property and once they occupy the unit they lived in, they'll be cashflowing.Again, this is part of a long-term play so most house-hackers don't see cashflow from day 1 in NY.

They gradually ramp themselves up to high fire or 100% based off the curve that was set by the installer.

If they have been good tenants I would gradually increase but vacancy is a killer and so can the unknown of a new tenant. 

The other 1/3 is in a rollover IRA which I’m gradually converting to a Roth.

I've gradually bumped my rents up so that there is enough leftover cash flow to fund any future turnovers.