All Forum Posts by: Andrew Everett

Hi @Seb Ko -- Your question prompted me to ask a follow up question. I'm very green on the STR requirements in Chicago so this is a rookie one.

From your post, do I understand that an investor can't set up a STR in a small multi-family (2-4 units) building? I see from the city's vacation rental fact sheet, the following, "In a building with 4 units or less, the vacation rental dwelling unit must be the licensee's "Primary residence" where applicant lives on a daily basis at least 245 days in the applicable calendar year." I feel like I'm missing something here???

@Darius Ogloza Thank you!

@John Warren Thank you for the advice!

Hi BP - 
My primary residence is currently on year 3 of a 15yr mortgage at 3.125%. I'm looking to buy my next home which will be a non home sale contingent purchase. My question is whether it makes sense to refinance my current home on a 30yr at 4.5-4.75% (as an investor + rates are ticking up) in order to cash flow as a long term rental. Is that additional interest really worth it over the life of the loan, just to get cash flow? On the flip side, I've always been taught to never have negative cash flow. Am I thinking straight? I'm between these scenarios:

1. Rent as-is with current 15yr owner occupant loan -- estimate negative cash flow

2. Rent unit with refinanced 30yr investor loan -- estimate decent positive cash flow

3. Sell property and deploy equity elsewhere -- have future investing goals of mult-fam buy and hold

Thanks!