@John Postma We are working with about 5 owners that are at the same stage as you with almost identical stories.

Proc. 2002-69, 2002-2 C.B. 831, for special rules applicable to husband and wife state law entities in community property states.

California's probate rules can be drastic in the event of death that having a proper estate plan in place can help in any number of situations, including if just traveling or incapacitated.These are all things you will want to discuss with your attorney and CPA.

However, if you sell instead of rebuilding, the IRS may include part of the payout in your taxable gain unless reinvested under the §1033 involuntary conversion rules, which allow you to defer taxes by purchasing a similar property within two years.If the property was your primary residence, you may exclude up to $250K (single) or $500K (married) of gains if you lived there for at least 2 of the last 5 years, likely resulting in no taxes owed.

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?

Each area has its own rules on how it works, but basically, you buy the house, pay a deposit and agree to rehab the house within a certain amount of time.

Some lawyers will file ejectment lawsuits and ask for service by publication, but that is not allowed under the rules.

Focus on buying below market value, running numbers first (cash flow, 1% rule), and choosing a landlord-friendly location with job growth.

Based in Tampa, I have a lot of knowledge in Pinellas County rules and regulations as well as best practices/highest returns. 

When it comes to housing, the FHA rules apply in addition to those of your state/city.