I have a large STR property that can accommodate 19 people, that has a hot tub.

Should you set aside additional money aside from capital gains to pay for the income tax increase if you make a profit on a property? 

House hacked a couple of properties here and it changed my life. 

If there are any NY market stats/comparisons, you'd like to see in the future, post a reply or shoot me a PM.Below is a quick Q3 comparison between this year and '23 for Suffolk County:Summary:- Single Family values continue climbing- Multifamily Properties are selling faster than last year - Market activity (sold properties) has remained steadyMultifamily sale prices have (slightly) dropped despite sales activity remaining similar to Q3 last year.

I get much more cashflow from distressed properties that I pay cash for and fix up to be LTR'S. 

Or buying a property in a seller's market, and then buying another one a few years later in a buyer's market.

I have a rental property.

Out of curiosity, which neighborhood is the property, and how is it performing?

Then that person sells the property to someone else and slaps a second on it. 

A tenant who fails to maintain a rental property could end up costing you more in property damage and court fees than the amount of rent they're paying you upfront.