No matter how long they've been doing this.

Many years prior to her passing she moved out of the home to live with another family and the home sat vacant for a very long time without anyone checking on it.

You want an accountant who can help you strategize and who is responsive when you want to know the tax consequences of the decisions you are making throughout the year.Good luck.absolutely, yes. we feel confident about filing, but absolutely ignorant to long term tax strategy! 

This would be our first rental and I think it could be a good opportunity long-term, but it feels like there’s some red flags here.

Matt, sorry it took so long to respond!

Thank you.How long does the STR permit usually take?

How long do you typically wait for a rental property to sit on the market before considering selling it?

I am NOT interested in owning any more real estate (retired here man) so I had planned on just paying my 15% long term Capital Gains tax rate and moving on to my "safe money" retirement program of MYGA's / CD's and High yield Savings account / Bonds / some Stocks.

and long-term relationships to help service my growing portfolio!

It is slightly under rented for the area just slowly trying to raise on long term tenants.