You can do a 1031 exchange and use those funds towards another investment purchase (basically a tax deferment).

Usually in the form of special assessments or ever rising dues/property taxes.

If you look on AirDNA, you can see similar types of homes that can earn upwards of $35k-$50k/year in revenue on Airbnb.

Prorated taxes (I understand this part)what other items that i should see on my closing bill?

I own my own business/LLC and am open to changing that structure for tax purposes, such as putting it under an S- or C-Corp if it would help with this situation.)I appreciate any and all thoughts on this matter as I can't seem to get out of my own head on this!

They aren't going to let a perfectly good vrbo income stream sit idle for long.Alternatively, you could try to find the house on various websites such as AirDNA, which should give you a rough approximation of what the property has historically earned. 

So many nuances from property taxes, insurances, what does airdna or rabbit say, cost of internet, HOA, permit costs, local utilities, are you doing maintenance or is someone else.... 

For our customers, they fall under our business license and tax.

They're like real estate taxes. 

And should they still file taxes separately or can they file jointly?