All Forum Posts by: Aaron Zimmerman

I would sell. Roll that equity into the next property and since it's your primary, you can exclude up to $500k in gain if married. 

Thank you for the analysis! Good to see Chicago has strong growth! 

I'd go option 2, provided the property cash flows upon move out or you plan to live in the unit for a long time. You can put less down which will keep your cash available. 

if you can, I would encourage you to max out retirement accounts and potentially do a backdoor roth if necessary 

If you're getting into the short term rental loophole, I'd recommend listening to some resources in the space such as short term rental riches and bill Faeth. Both have great podcasts. 

from a personal finance perspective, I'd recommend looking into financing options with lenders. After that, learn more about the STR loophole such as material participation, 7 days or less rule, and personal use days. From there, reach out to a CPA to ensure you're implementing the strategy correctly.

I would probably house hack each year with the funds you have until you run out of money. You can easily buy several nice properties at 5-10% down. This is by far the easiest way to get into real estate from a financial perspective 

I would agree to not take the money out at this point until you have a deal in hand. I'd look to consider moving some of the monies into a money market.

additionally, you're probably getting back more like $130k. Penalties are 10% plus marginal tax rates for fed plus state. That could easily be 30-40%. 

instead, I would consider taking a loan against your 401(k) and pay the money back to yourself. You can take up to $50k or 50% of vested balances for most plans 

I would check out renovo. You can check the straight up Chicago investor website. He's very well known in Chicagoland area 

@Christopher Mooney - what does your real estate portfolio look like? Regardless, I would definitely recommend exploring the advisory side in addition to the prep of the return. There are often things I point out that my clients aren't aware of or haven't considered. 

My recommendation is for you to look for someone that does is a real estate cpa that does prep and advisory. As for finding CPAs, I would look at the forums, ask local investors, and use the find a tax pro finder that BP has 

It is Absolutely possible to find a CPA that services you for both your real estate and personal needs. It's generally included in the price for services.

Local does not matter, most RE CPAs will be able to service your needs from afar and most communications are digital anyway. I would recommend looking through the BP forums and reaching out to a few people or using the tax pros finder. 

@Sarah Marium - welcome to BP! It is Absolutely possible to cash flow with 25% down in Chicago. It just depends how much cash plus available reserves you have. The questions I would have for you are: 

1. are you willing to house hack? If yes, you can put down a lower down payment. 

2. How much will you be able to save towards your goals on a monthly basis.

3. how committed are you to cash flow? Are you willing to do an MTR or STR as needed to boost cash flow? In todays market, you need to make deals pencil.