We bought a Chicago bungalow in Oak Park a year ago and spent a lot of time and money making into what we hope is a perfect mixt of charm and modern amenities.

@Lady Cerezo Keep Jersey City in mind too its way cheaper than NYC with some really nice neighborhoods that have a lot of the amenities of the city and you’re only a quick train ride away from Manhattan.

It helps if you have a well-located, super clean, well furnished / eclectically decorated, comfortable property with creature comforts and amenities.

The rules are more amenable to people with active businesses (payroll, expenses, etc...) than investors.

The indoor basketball court isn’t the only amenity to get your pulse racing.

Set high minimum days for stays during peak season and peak events and 2 day minimum stay during off season.Check amenities with your competition and make sure you offer comparable or better ammenities.Try and have same day check in and check out instead to maximize revenue instead of worrying about charging more for late or early arrivals.Have a Pet friendly house and charge pet fees.

@Mark Wurtemberg Zillow is a fair place to start, zestimate can be a rough guide is you are realistic about the amenities and finishes. 

The lines will be running right near Colorado which has lots of amenities as well which makes them even more desirable.  

Check the finishes of these houses and see what they offer in terms of amenities and try to pick the closest ones that match the subject property when it's finished. 

Proximity to amenities, shopping, schools etc.