I've been seeing a lot of posts here (and on Reddit and other real estate forums) from landlords asking whether they should self-manage, hire a property management company, or how to handle specific situations with tenants.

I've been in property management for a little over 23 years, and I also own a fairly large portfolio of residential and commercial properties myself. Over the years, I've made plenty of mistakes, learned a lot of lessons (sometimes the expensive way), and seen just about every situation imaginable.

I thought I'd put together a few things that have helped me over the years. This isn't meant to be the "only" way to do things.  There are plenty of successful DIY landlords out there, and there are also some outstanding property management companies. Both approaches can work.

Hopefully, this helps someone avoid a costly mistake or at least gives newer investors another perspective.

One quick disclaimer before diving in: my experience is primarily in New York (including NYC, which is basically its own world when it comes to landlord-tenant law), New Jersey, Connecticut, Rhode Island, Massachusetts, and Pennsylvania. Every state, and sometimes every city, has different rules.

For example, Newark and Edison are both in New Jersey, yet they each have local ordinances that can affect how certain situations are handled. Connecticut is fairly consistent statewide, but I wouldn't assume that's true everywhere.

With that said...

1. A Real Estate Agent and a Property Manager Are Not the Same Thing

This is probably one of the biggest misconceptions I see.

A good real estate agent can be an incredible resource when buying or selling property. But unless they also manage rental properties, property management is an entirely different business.

I've heard advice like:

 "Just make the seller deliver the property vacant."

Depending on where the property is located, that may not even be legally possible.

In much of New York, especially municipalities that have adopted Good Cause Eviction, and throughout New Jersey under the Anti-Eviction Act, tenants generally can't simply be removed because ownership changes.

Even owner occupancy has different rules depending on the property type and location.

Likewise, most landlords can't simply terminate a lease early because they changed their mind. There usually has to be a legal basis or mutual agreement.

The point isn't that real estate agents don't know what they're talking about; they absolutely do in their area of expertise.

It's just important to remember that buying and selling real estate and managing rental housing are two very different professions.

For legal questions, a landlord-tenant attorney is almost always the best resource.

Ironically, after 23 years, I've had attorneys call me asking how certain situations typically play out in practice. Law and real-world property management don't always look the same.

2. Cash Reserves Will Save You More Than Once

If I could give only one piece of advice to a new landlord, this might be it.

Have cash.

Then have a little more.

Every landlord eventually gets hit with something expensive.

A roof fails.

A sewer line collapses.

A boiler dies in January.

A tenant skips out.

A vacancy lasts longer than expected.

An eviction takes six months instead of six weeks.

If you're relying on credit cards every time something goes wrong, real estate starts becoming stressful instead of enjoyable.

Personally, I like keeping around six months of operating expenses in a high-yield savings account dedicated strictly to the rental properties.

Everyone's numbers will be different, but if your properties generate around $6,000 per month, I'd want roughly $30,000 available without having to borrow it.

This year alone I've spent roughly $140,000 on turnovers across three buildings.

Was I thrilled about it?

Absolutely not.

Was I able to sleep at night because the money was already sitting there?

Absolutely.

Reserves buy you time, options, and peace of mind.

3. Build a Team Before You Need One

The worst time to find a plumber is when water is pouring through the ceiling.

Every landlord should have a bench of reliable professionals.

That includes:

- Attorney

- Plumber

- Electrician

- HVAC contractor

- Roofer

- General contractor

- Handyman

- Insurance broker

- Accountant

Even more importantly...

Have backups.  People retire, contractors get booked out, someone gets sick, someone stops answering their phone.

It happens.

If you're hiring a property management company, ask questions.

Who actually performs the maintenance?

Do they have employees or is everything subcontracted?

Will you receive multiple estimates?

Do they mark up invoices?

Will you see receipts?

Transparency shouldn't be optional.

You should always know where your money is going.

4. Protect Your Privacy

This one doesn't get discussed enough.

Whenever possible, I prefer not to live in the same property that I'm renting out.

If you do, I'd recommend treating yourself like any other tenant.

Maintain professional boundaries.

Separate your business from your personal life.

I also recommend using a dedicated business phone number, business email, and a separate mailing address whenever possible.

Yes, someone can usually figure out ownership through public records if they're determined enough.

Most people won't.

There's no reason to make it easier.

I've also had good experiences using services like DeleteMe to reduce the amount of personal information available through online data brokers.

Nothing is perfect, but every additional layer helps.

5. Insurance Is the Cheapest Thing You'll Ever Be Happy You Bought

This is one area where trying to save a few hundred dollars can cost you hundreds of thousands later.

I generally recommend buying insurance from financially strong carriers with an AM Best rating of A or better.

Personally, I've had good experiences with Chubb, USLI, and Erie.

Military members and certain government employees may also find excellent coverage through USAA.

Everyone's risk tolerance is different, but I usually suggest discussing at least $1 million per occurrence, a $2 million aggregate, and an umbrella policy with your insurance professional.

Here's why.

A couple of years ago we took over management of a six-unit building in Hoboken.  The owner had owned it since the 1980s.

He'd never had a claim.  Never had a lawsuit, and he thought everything was fine.

We convinced him to increase his liability limits and purchase a $2 million umbrella policy.

A few months later, someone claimed they slipped on the sidewalk in front of the building.

In Hoboken, property owners generally have responsibility for maintaining the adjoining sidewalk.

No cameras, no witnesses...  Just one person's word against another's.  The lawsuit dragged on for quite a while.  Thankfully, he had increased his coverage before everything happened, and he ultimately prevailed, but the process was incredibly stressful.

We later added exterior cameras around the property because those few hundred dollars in equipment could save tens of thousands in legal expenses if something similar ever happens again.

Real estate has been very good to me over the years, but it has also taught me plenty of lessons; many of them the hard way.

There isn't one "perfect" way to be a landlord.

Some people successfully self-manage hundreds of units.

Others hire great property managers and never look back.

The important thing is building systems that protect your time, your money, and your sanity.

If this post is helpful, I'm happy to put together another one covering topics like tenant screening, lease enforcement, handling difficult residents, budgeting for capital improvements, working with contractors, or evaluating a property management company before hiring one.

I'd also love to hear what's worked well for everyone else. Some of the best ideas I've picked up over the years have come from conversations with other investors.

Take care all.