All Forum Posts by: Aaron Zimmerman

I would say when my first property really started to cash flow and not be a headache. It took a couple years but was well worth it !

@Asma Kabeer I'd encourage you to go to some amazing local meetups in addition to posting here. I'd consider going to some of the NBOA events, Chicago multifamily club, Windy City REI and much more!

@Gin Zhuang due on sale clause is definitely tricky. The better way to do it is It reach out to your bank and see if they'd allow you to do it . Better to ask for permission than beg for forgiveness on this one. I've had a couple of my clients successfully do this by asking first and explaining to the bank what they were looking to do 

Welcome! I think house hacking is a phenomenal strategy to get started. This is by far the lowest entry point with favorable down payment. You'll learn a ton and then you can repeat the cycle. If you buy one a year or every other year, you'll be thanking yourself later! 

I would agree with Micah. 2-4 unit would be the way to go for house hacking given you want separate living spaces. The goal with the house hack is to reduce housing expenses when living there and cash flow after, even if slightly positive. Keep in minds, rents should increase which will boost cash flow. 

Have you considered doing medium term rentals? 

for the STR, you need to look at average stay. So long as the average is under 7, you're in the clear provided you've met the other requirements.

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.