Unless you give up on being a landlord immediately, you’ll be faced with renting out a property after you have already have had it rented out. This presents a different set of problems than, for example, having your own house up for sale. With your own house, you know that you can keep it clean and tidy (right?) and accommodate showings. You have an interest in getting your house sold, so it’s worth the effort.
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Having a tenant-occupied property is different. Getting a tenant in quickly after their departure is not high on their list. They will be packing for their move, living their lives, and not want to be bothered. But you’re anxious to line up the next tenant. The longer that the property is empty, the more your costs add up (utilities, carrying costs like taxes and mortgage payments) and your profit goes down (no rent collected).
So what to do? Here’s some things to consider:
First, what are the laws and customs where you live? Are you even allowed to show the property to potential renters while it’s still tenant occupied? What does your lease agreement say? I always make sure that our lease agreement specifies that, in the last month of the lease period, realtors are allowed to show the property and a lock-box will be placed on the door.
Second, what condition is the property in? Have the current tenants taken care of the property? Has the yard been taken care of? Is it neat and clean inside? If the house doesn’t show well, you could be doing more harm than good. No one will want to rent it out, or pay what you’d like. Not only are you giving those people (and their realtors, who may be in a position to show it in the future) a bad impression, but your property will be on the market those 30 days, plus the time that you need to make it right. People will start to wonder why it’s been on the market that long. They’ll try to get a reduced price.
Third, how nice and cooperative are the current renters? What have your experiences with them in the past taught you about them? Are they usually cooperative and friendly? If you think that they will turn down every showing, you again are only harming yourself by having it on the market without activity. Sometimes you’ll have a good idea if someone will make an effort to accommodate showings and keep the place at least presentable. But you could be wrong. I once had a perfectly nice woman renting a property, and I thought that she’d be fine with showings. She said that she’d be fine with showings. She turned down every showing opportunity, and, one time, when some people did show up, yelled at the them to “get out” and chased them out the door! There’s nothing that we could do about the cancelled showings, so we lost that month.
Fourth, do the current renters have a good impression of you and the property? I’m hoping that they do, but sometimes they won’t. I had one couple that I really got off on the wrong track with, right from the beginning (a misunderstanding, but still…). I knew that I could not list the property while they were still there. If they were home while a prospective tenant came by, who knows what they might have said!
Similarly, is there some sort of aesthetic repair that needs to be made? One time we had a leak in a property. Of course we repaired it right away, but there was drywall damage left. The renters (who were the nicest people ever) asked that we wait until they leave just a few months later, so that they would not be bothered by the mess. I agreed, without thinking about how that affected me: I was not able to show the property until after they left and the damage was fixed.
You might think that you could, for example, leave a note stating that work would be done as soon as the tenants move out (or perhaps the renters are already out, and you’re busy working on repairs), and that people walking through the property would be able to adjust their thinking and be o.k. with that. You think incorrectly. Potential renters have no imagination, and do not trust such statements. I’ve had people interested in my property asking me about the very things that I left notes about. Yes, we’re repainting. As stated on the note prominently posted on the entry wall, and which you can likely tell by all the painting equipment everywhere. Yes, I’m glad that you like the new counter tops that were just installed. We are putting in sinks and faucets, thanks for asking (I’m not kidding!). Real situations, with sarcasm withheld in real life.
Your goal is to show the property in its best light. Do your best to balance the pros and cons of showing the property while it’s still occupied. Sometimes the answer will be easy: you need to wait. There’s no way you’re showing the property as is. Or perhaps you simply can’t afford to wait, or the place looks wonderful already. But for those in-between situations, think about the market, and weigh the pros and cons.
The Blog About Being a Landlord 
Nicely covers the subject!
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