I purchased a SFH back in 1995 for 220,000. Lived in until 2001. Converted it to a rental in 2002. It's been a rental ever since. Renting for $3650. House is valued close to 1.5 million. Should I sell or keep it as rental?

I would keep it and your rents will only increase while your tenants are buying the property for you. My tenants paid for the properties I own. They have canceled checks and I have paid off mortgages.

Questions to ask yourself;

If I sold it how much would I NET after capital gains tax, cost of selling (relator fees, advertising, staging etc), would I have to pay to get the tenant out.

Am I renting it for what is Fair Market Rent? (at a value of 1.5 million, I think you are below market. I am getting $2500 to $2800 on half million properties)

Would the value of the NET of the sale be able to bring in as much or more as the value of the net cash flow of the FMR less expense? Only you can truly answer that.

Talk to a good financial advisor who can ask you enough questions to understand your position. Make sure the financial advisor understands real estate. I talked to 6 good, well respected financial advisors before I found one who really understood real estate.

You are currently getting about 3% return (before expenses) on your money. $3650/month rent for 12 months gives you a gross rental income of $43,800/year. Property taxes, insurance, maintenance, repairs, and property management will typically cost about half of your gross rental income. After expenses, you might be left with about $20,000/year in net rental income, or, 1.5% actual return on the $1.5 million asset.

Do you enjoy being a landlord and do you want to have more investment real estate? If you want more real estate, do you want to borrow money to expand the real estate? Or would you prefer to have the money invested in the stock market? The S&P 500 index funds have historically done about a 10% annual return.

The 10% return from the stock market is a lot better than what you are getting with the rental.

Welcome to the Sellers Club.

Your return on investment is excellent, but your return on equity is terrible. If it were me in this scenario, I would sell and redeploy the capital more productively.

Just to give you an idea, with $1.5 M in proceeds.... assuming a 1031 exchange to shield from taxes and recapture... I could probably find you property producing around $10,000 in monthly income WITH a competent, reliable, trustworthy professional property manager in my area.

If you want higher monthly income, sounds like a no-brainer to sell.

Without knowing what you are considering for an objective, it is hard to give you any valid help.

a land trust could yield you extra cash if you could prevent the resetting of the assessment value, but the time to do that would have been a couple of years before the sale of the beneficial interest in the property.