Challenges?

-Opportunity cost: A 7% interest rate isn’t great, but if you think you can achieve returns higher than 7% by buying another cash-flowing property, paying off the mortgage might not be the best use of funds.Now, let’s explore saving to buy another property:Investing in a Second PropertyPros:-Diversifies your portfolio, reducing risk if your Palm Desert STR underperforms or faces challenges (e.g., stricter regulations or lower demand).

Its not widely covered but Wright in the 2nd half of his life was completely consummed with the challenge of providing low-cost and beautifully designed homes to the countries working class.

Challenges?

." - which to me indicates the same doubts that I have about the legality of the IRS position.Until the IRS is challenged in court over this position and loses, I choose to comply with their position.

Not having experience qualifying prospects I would think that the leads you would get from here, if any, would be..... challenging. 

Quote from @Michael Smythe: Besides MANY self-labeled "gurus" exaggerating their success, many of them just supply readily available info.If you're too busy to find the info and are willing to pay for it, no problem as you accept their time vs money solution.REGARDING S8 GURU ISSUES SPECIFICALLYMost of them don't share all the facts about how Section 8 actually works.They claim you can get HIGHER rent from S8 tenants vs private-paying tenants.Why would the government allow our tax dollars to be spent this way?

Challenges?

I think the unsuccessful and struggling units who have not jumped ship yet will continue to do so, leading to less supply, increasing demand, and a better year for the successful units. 

Hi @Jacob Dalton,Thanks for sharing your situation—it’s clear you’ve put a lot of thought into this decision, and I can understand why you’re concerned given the challenges of being a landlord in Cook County.Screening tenants is definitely a key step, but I agree it’s not foolproof.