Investor · Milwaukee, WI · Member since 2018 · 16 posts · 8 votes
Hello everybody!
I am looking to move out of Milwaukee soon and I think my current home would do very well for a short term rental here in Milwaukee around the Bay View area.
Is it worth getting a property management company to do all the work for me?
If so, does anyone have any suggestions or recommendations?
CPA · Milwaukee, WI · Member since 2016 · 2k+ posts · 1k+ votes
4y
@Nathan Simons
John is right. Outsourcing the PM will take a big chunk out of your bottom line. However, self managing could potentially take a big chunk of your time.
Speak to a reliable PM like @Chaim Lampert for more info. 
CPA · Milwaukee, WI · Member since 2016 · 2k+ posts · 1k+ votes
4y
@Nathan Simons
John is right. Outsourcing the PM will take a big chunk out of your bottom line. However, self managing could potentially take a big chunk of your time.
Speak to a reliable PM like @Chaim Lampert for more info. 
Architect · Memphis, TN · Member since 2020 · 259 posts · 144 votes
4y
@Nathan Simons The above comments have some merit. However, I challenge you to interview some great property managers in your desired area. Questions to self: What does this company provide me? What is it that they provide me that I did not think about? Can their services justify me spending the money for their expertise? What did I gather from these interviews? Etc. Then vice versa.
To answer your question, you consult with owners who has only used property managers, owners who has only managed themselves, owners who has both managed and hired a property manager, read articles, check social media platforms, or anything else that could be helpful. The broad term for these things is “sources.”
And, usually, once you’ve done the research, you present or summarize it in some way. In many cases, this means writing the pros and cons or another type of review process, but it could also mean testing the water doing one or the other (management company or self-management).
Do not get stuck in believing any of our experiences will be yours.
Very curious to hear how you work through this! I've been looking into potentially doing STR in the area with one of my duplexes as well (Brewer's Hill) and have thought through how a hybrid approach might work best for me.
The 2 team members I believe you need to execute a hybrid approach would be your cleaner and handyman. With these 2 people, I believe that there are many tools and process examples out there where you could run this remote while leveraging others. On the flip side, you may not have the economies of scale to make paying for those time saving tools a good investment.
I haven't tried this myself but am wanting to give it a try!
Professional · Milwaukee, WI · Member since 2013 · 52 posts · 25 votes
4y
Hi Nathan
I work with a PM company based out of Bay View, Performance Asset Management. Our model is built and focussed on long term residents (3-8 years).
I have friends and colleagues that go the STR route with great success but this comes with a heavy DIY time investment and strong/reliable local relationships with contractors and cleaners.
One company I can suggest that manages STR's would be StayMKE
Feel free to DM me anytime to discuss Long term rental and management if you ever want to explore options.
Rental Property Investor · Oconomowoc, WI · Member since 2016 · 996 posts · 431 votes
4y
Whether you are purchasing a long-term rental or STR as an OOS, whether you need a PM is going to primarily come down to your network in the area. You can rent it out remotely, manage most guest complaints remotely but you may still find you need "boots on the ground" from time to time. Depending on who you get in your network, will your cleaner let you know of the damage that should be charged to the previous tenant? Do you think they can reliably do that? If the TV dies and needs to replaced, are you going to pay a store like Best Buy to deliver it, and if they require someone there...who's going to sign? How quickly will they be able to deliver it versus your "boots on the ground".
I'm not necessarily advocating for using a PM on STRs but you need to think it through clearly because unlike long-term landlords who don't get rated by a lot of sites, your guests will be encouraged to leave a review with whatever booking site you use. If you are going to get bad reviews, you don't want it to be for things that could have been more easily addressed if you had steady boots on the ground (whether a PM or not).
Everyone above gave great advice on choosing whether or not to self-manage or outsource. I always make that decision based off of my personal/business goals.
If you are still trying to achieve financial freedom and escape the rat race, then you may need to put in the time to self manage and keep that bottom line healthy, so you can reinvest in other assets.
If you have already achieved financial freedom and want to spend your time doing activities that you want to do, then perhaps sacrificing that % to outsource makes sense. I strongly believe having boots on the ground in the local market is a huge value add. You can either develop those relationships locally (putting in the time yourself) or go with a PM company who already has a team in place.