Until / unless you are 100% positive you can DIY, you need management. And most property managers suck. So you need to carefully vet, get recommendations and ask a lot of questions especially about screening, maintenance, collections, evictions, so much more.

You need to get with your financial advisor CPA tax person first. You probably will want to put your properties into their own LLC but you need advice re every financial implication.

Those are the basic basics. If they haven't run screaming at that point, then start finding them properties. But put the fear of God in them first. It can be profitable or it can break you. And it can fry your nerves real quick.

Find out whether they currently have a rental or they are a newbie.  Nothing is wrong with newbie but I know there are more time and hand holding and education involved.  Finding a good tenant who will pay on time and take care of the property is not easy.  Here in Dallas during summer if the AC is broken he needs to find somone to fix it asap.  They many ended up having to pay tenants their hotel room.  They may also need a property manager, consult with an attorney and CPA.  I think the bottom line is lay everything on the table, good and bad, and let them decide whether they'd like to continue or not.  

let them know that it can be a great investment, but being a Landlord is not for everyone.  I had an Instructor once who claimed in order to be a Landlord, you need to be able to evict a widow and her three children on Christmas Eve.  Perhaps a *slight* exaggeration but a lot of truth in that statement.

Have a company handy to run credit checks. Know the laws on evicting deadbeat tenants. 

I'm very upfront about the amount of work, time, and worry it may entail, and I always have a great property management referral on hand if they're not up for it.

The answer is longer than I can post here.  It is a long discussion. Beyond the real estate and management side of the equation, I always tell them to consult with the CPA and/or financial planning advisor as well. 

Why?

What's your goal?

What's your plan?

Self Manage or Property Management Co?

and about 25 more questions...

    Long discussion. 

    This is a great idea, investing in rental property is one of the best ways to create and preserve wealth.  Having said that,

    What are you trying to achieve?   Are you looking to buy a single family, duplex, quad, or an apartment complex?

    Have you, or a close relative or associate, ever been involved with rental properties?   

    Have you met with your CPA about the financial ramifications of investment property? 

    Are you familiar with the Florida Landlord Tenant Act (F.S. 83)?   

    Will this be DIY, or do you intend to use a property manager?   

     Have you talked with your Insurance agent, about insurance on the property, and general liability? 

     Etc. etc. 

Watch the movie Pacific Heights !!! Then hire a Professional(full service) Property Mngr. !!!!!!!!!!!!!!!!!!

I don't even want to think about those days... I use to own many units and managed all of them myself... but I got away with alot in those days!!! laws have changed.... I can't take a front door off if they owed me  money!

To think long and hard about it before they do anything! And before they get too far down the road, we see if the numbers will actually pencil out.

Steve Penner I educate them the ins and outs of owning rental properties. Then I send them to their CPA to learn about the tax implications of ownership.

Have a business plan and your financing in place before any purchase.

Candice A. Donofrio gave you a great answer. If they want to purchase a rental, I share experiences with them from other investor clients. Some people are cut out to be landlords, others, not so much!

You have many great answers here Steve Penner 

Candice A. Donofrio gave you the perfect answer.  It is amazing how many think this is EASY without have a reality on their numbers.  A

Learn how to manage, read the horror stories, get on Bigger Pockets, learn how to do background checks, find good contractors... or higher someone to do that for you.

Luckily I work wirh smart investors.

Kathleen Daniels summed it up well. The conversation can indeed be a long one specific to the caller

If they do not currently own rental property (my first question)... I ask them "why" they want to own investment/rental homes? Many have false expectations of true revenue and a reality check slaps them pretty quick after a conversation. If they understand or are open to the realitsic dynamics;  the amount of work managing themselves or;.. the good, the bad, the ugly of PMC's then time for more education. I give them insight as a property investor and have them speak with other investment owners is a good idea. If they are still interested, on to the next phase... more education, blogs, detailed estimated ROI to go over and of course suggest/discuss the importance of establishing an LLC.

It is sometimes easier to talk to them while looking at homes. That way they can see. I can add insight, ask questions and let them know what they are in for if they are new investors. 

Find a good property manager!

Run!    LOL

I ask questions to find out how much experience they have and what their exit strategy after they buy a property, after that we develop our plan and follow it. 

I have been one for a very long time, I would offer to coach them.

Steve Penner - it is not for the faint of heart! You must have a thick skin....

I suggest we meet and that is when I find out if they are a bonafide buyer for rental property.

I show them what I go through

Consider a property m

I would recommend that they use a good property management company.

Hire a good professional to manage it....

Hire a good property manager

I do not work with many investors, not my niche, but I have had a few, and make sure they have a good nest egg, just in case.

in my market it's short term rental and there is great money in it.  I tell them the management company I recommend and the cleaning service I recommend.

Candice has answered