But if the market for large STRs is thin, the basement might not add substantial value.Selling: Selling could free up cash for other investments with better returns, especially if you’re uncomfortable with the low ROI and management required for STR.It’s a tough call, but if STR potential is there, it might be worth a trial period to see actual cash flow before committing fully to the basement investment.

To name a few factors: your time commitment, ability to focus on marketing & sales, your network...As a current business owner, you may already have a pretty good starting point.Most agents close 1-2 deals their first year (if any)...

Please at all costs do not commit mortgage fraud based on the advice of someone who will deny they ever spoke to you about any such thing if all hell breaks loose

Balancing job and investing stress requires prioritizing properties and strategies that align with risk tolerance and time commitment.

Premium increases are rippling through the market; the state is also always going to be financially strapped/high tax due to union pension commitments from past generations and the high tax, high services nature of Chicago.I'd highly recommend getting on a plane and driving around before you buy anything there. 

The key to navigating this market successfully is to stay vigilant and committed to this niche for the long term.

Additionally, make a commitment today to at least spend a few hours a day learning about real estate investing.

Depending on your loan structure I'm not even sure you could legally offer a personal guarantee outside of the loan for that money without committing mortgage fraud, as anything that could hinder the ability of the primary lender to recover their principal is supposed to be declared during their diligence period, and any material changes up to the point of taking the loan are supposed to be disclosed as well.

The time commitment the HH properties took from our company made them simply untenable to continue to manage. 

In fact, now may be the best time of the year to buy properties due to reduced buyer competition and seller motivation (those selling now are probably committed.)