All Forum Posts by: Conrad Legé

I own and manage a few STR units in Chicago & looking to scale in new markets this year. What is your process when sourcing and furnishing new units remotely? What are some important things to consider?

Hello all,

Like most people in Cook County, my property taxes have climbed higher again this year. I received something in the mail from a tax attorney about appealing my taxes to potentially lower them and now am considering it for the first time. I've owned my rental property for two years now. Has anyone successfully done this? Am I able to appeal myself? Also, I realized on the cook county assessor website my property valuation seem to be very undervalued. What are the risks of appealing? Could I see my taxes go even higher if they reassess my home? Looking for insights from those have gone through this process. 

Thanks,

Hey all,

I operate a STR management company here in Chicago. For 2024 I am looking for STR arbitrage opportunities in new markets, South Florida/Miami being one of them. I am looking to partner/connect with folks in the Miami area who know the market. Also, considering hiring an VA to help source & secure these units. Anyone have experience with VAs in this fashion? What are some things to consider in regards to setting expectations, milestones, etc. Appreciate any insights.

the ROI on dynamic pricing will be more realized once you take advantage of economies of scale and are managing multiple units. One, the pricing of the software goes down as you increase your units, two it will provide more consistency & accuracy with your pricing as oppose to you trying to manually adjust pricing for 20 different calendars.

@Richard Elvin Your analysis doesn't even include turnover (cleaning) costs or utilities so that return is actually much lower.

I would avoid homes that are within a HOA; they rarely allow STRs. Target single-family or multi-family properties. Again, understand the local ordinances.

Here are a few strategies source properties:

1. Hire a VA - these can be found in STR & RE Facebook groups

2. Networking - go to local real estate meet ups in your area and meet landlords & others in the industry 

3. Go on Zillow and reach out to landlords whose properties have been on the market > 45 days

I use Hosthub for multi-channel management and PriceLabs for dynamic pricing. I also have my own STR management company based out of Chicago.

From what I understand you can only deduct up to 50% of total expenses if it is a primary residence. However for your particular, situation its best you consult a CPA with real estate experience for these matters.

I started off with Arbitrage in 2019 then bought a building and turned one of my units into an STR. Great strategy to bring in high returns and cash flow & easier to scale. Its a more saturated market now due to low barrier to entry and all of the "guru's" selling Arbitrage online to folks. However you can still make money doing it, its just not hand over fist anymore. Just make sure you understand the STR regulations in the city you plan to Arbitrage in.

I furnished a 3br/2ba condo for under 6k back in 2019.