Though, if your client base is nice retired people, it probably won't matter.  

This is also apparently going to "be a thing" with airbnb portfolios as I am currently working with another owner ready for retirement.

Currently I am looking to buy and hold for the long-term with the goal of being free and clear by the time I retire ~20 yrs. 

The old guard gets burned out and retires.

We are retired and I have to convince my wife.    

This provides extra peace of mind in case your upleg does not work out or the seller or lender will not deal.4) Truly retire for real estate ownership.

I'm Benjamin from Munich in Germany and very happy to have found this thread.Having always been a fan of Lisbon, I'm excited I convinced my parents to retire in Portugal and buy a home in Estoril last year.Now it will be quite practical for me to combine work/invest with pleasure and visits.

This allows for proper retirement of assets.If a property has already been sold it may still be a good candidate for cost segregation as long as you sold the building and have not filed the tax return.

I have tried to do a HELOC but I’ve recently retired from the military and haven’t started another W2 therefore lenders don’t want to approve the HELOC.

And it is not something you do retroactively anyway, only proactively.Contribute to retirement plans.