They could self manage for several years, using the rental income, until the next phase of their retirement.If they have a decent amount of financial discipline, they may want to get a HELOC now before they build to get the most favorable rate.

But I favor higher returns, even if they come with higher risk.Obviously, you're on the other side of the spectrum.I don't care.

I'm in favor of a higher bar before posting but I think it's a minority position. 

If cash flow improves, it might make sense to hold onto the property while expanding your portfolio with new acquisitions.Reinvestment OptionsIf you sell or pull equity, focus on markets and property types that align with your cash flow goals:Out-of-State Markets: Research markets with strong rental demand, favorable landlord laws, and higher cash-on-cash returns.

A mix of short- and long-term strategies could hedge against market shifts.Borrowing allows you to scale faster, especially if you can secure favorable terms.

Last but not least....A few members in replies have already mentioned why it makes sense to hold…….I very much appreciate ALL FEEDBACK, however I think it will be helpful to provide some added context as to why I am absolutely certain (and my CPA’s are convinced as well) on my decision to liquidate the entire portfolio and onceAs I educate clients on daily, income tax brackets as well as long term capital gain tax brackets in our country are more favorable right now than they've been at any point in the past 80 years.

Each week, I analyze the MLS, exploring cities and towns across South Florida to identify areas favorable (or not) to short-term rentals.

I would not favor one or the other. 

I am having problems finding DSCR lenders with favorable terms in Florida. 

I don’t place all the blame on him, as I understand Massachusetts law is heavily tilted in favor of tenants.