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My tenants were used to paying cash, since the property manger used to live near by and would go collect.

I live in Chicago and have a condo unit in Scottsdale.

My plan is to live in the house while in the area and either rent it or sell it once I decide to move.

You live your best life and get some rental income.

I'm at 2200 Sq ft with 3 bedrooms, a major living room, and a climate controlled finished Florida room. 

Ideally I want to buy something in Florida that I can keep part of the property vacant for me to live in several months every year.

I have a 2bd 2 ba vacation rental worth of furniture supplies, living room, kitchen, laundry room everything you would need turn key for a airbnb or VRBO where is a good site to sell it all in one and not dirt cheap? 

I have cleaning services and handymen/contractors and live near the property. 

Like a PM said a condo across road from the beach only generates 30k revenue  but my sister lives in a neighborhood 30 minutes from the beach and the owner of a house next to hers claims it pulls 60k....