Given that I'm not positioned to buy just yet, and simply running the numbers, is there a rule of thumb for estimating insurance costs that would make sense in Cook County?

Folks having been buying real estate without a Wyoming LLC for a long time......

Would this be a good opportunity for someone looking to buy/hold? 

I’ve seen people buy land thinking water was covered only to find out they had to pay 6 figures to get water re-routes or upgrade pump stations.

He’s only 55, he can enjoy his retirement, golf, etc for a few years and buy back in when he sees a good opportunity.

If you have some capital, income, and decent credit, buy a 4-5 bedroom house and rent bedrooms. 

We aren't the traditional flippers who run in, throw up a lick of paint, hide the disastrous side of things and essentially trick people into buying a lemon.

You could also get a line of credit for about $150k (you should be able to borrow 75% of the value.)The reason I suggest this is…1) you save $40-$60k in selling costs. 2) you have a lower blended interest rate (2/3rds at 3.25% and 1/3rd at 7 or 8% instead of the whole $500k at 7 or 8%) saving you another $1k/mo in interest. 3) you only pay interest on that $150k when you actually use it, not from day 1  Unless you hate this property, or want to buy something you can’t afford without selling, that would be my plan.

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

If you have access to private equity then sure, but if you want to buy properties yourself then at best you are looking at 1-2 per year if you have really good income. 3.