All Forum Posts by: Aaron Zimmerman

Welcome Jerome! Seems like a solid plan. I would look to leverage w-2 income as well. Consider house hacking and partnering with people to maximize your financial position so you can keep acquiring buildings! 

@Todd Goedeke it depends what the objectives are. Generally with short term rentals, assuming similar income from year to year, you'd want to keep buying short term rentals by rolling the tax savings (deferral) into another property 

Either way, assuming even one year of self management, you still have to get through the year. 

My comments stem from people jumping into short term rentals and not realizing the commitment level involved to do it well. 

Totally agree that investors can outsource to a PM company. That said, you're often given up 10-25% of gross rental income for this privilege 

@Michael Plaks I would agree. My comment assumes cost seg is being done in 2028. If no cost seg, then you're 100% correct. 

@Grady Schmidt - welcome! I'd encourage you to go to some local meetups, listen to the straight up Chicago investor podcast, and stay active on BP. Feel free to pm if you'd like to connect and I'd be happy to point you in the right direction for some resources. 

@Syed Ahmed is spot on. I'd be looking to get under contract in December/January and close in January/february. You may have some holding costs but you should be able to fill up your unit by end of March/April at the latest. I would encourage you to think long term about tenant placement. You don't want to take on the first potential resident especially if they're marginal. You can also have a longer lease term too so the next lease ends during a more peak month to rent

There has to be a nicer part of the city that perhaps is not c class. That's where you'd want to invest. Totally support the multifamily desires. Best of luck!

Everyone has addressed the key facts above. A couple points I would add:

1. You want to figure out if you can utilize the property's losses. Perhaps you have other properties that the losses could offset or you have gains on this property and have losses from other properties.

2. In 2028, you may get a substantial benefit. Since the property was PIS in 2023 and you'd be looking to do the cost seg in 2028, most of the 5 and 7 year useful life assets will be mostly depreciated anyways. 

3. I would ask why you're looking to convert it into A short term rental? Is it tax Benefits? Cash flow? If you don't have the right temperament for this, it 's probably worth keeping as an LTR assuming it cash flows 

@Andre Taylor - please pm me and I can provide several quality providers that operate in the Chicagoland area. 

Thanks for sharing Paul! Much appreciated for providing this analysis! It's good to see the areas near downtown making a bit of a comeback. 

Reese - great plan! House hacking is the way to go. As a former house hacker, it's a huge stepping stone to leap into real estate. I'd recommend doing it as often as possible!