However, it's a safe bet that these respective areas will continue to appreciate steadily for the reasons noted.

However, the broader structural issues of affordability, housing supply, and financing access will continue to shape the market in the years ahead.For now, the homebuying process remains a challenge for many in this generation.

Additionally, we have a decent amount invested in retirement accounts, which we plan to continue building over time.As part of the move, we’ll be purchasing a larger home.

This is a question that has come up a million times and will continue coming up forever in Chicago unless eventually things change one way or another.

For instance, if he paid $40,000 to buy a house and sold it for $80,000 with $10,000 down, he could keep $10,000 in reserve  and tap into it to hire attorney, file eviction case , remove defaulting buyer/tenant and continue paying off investor loan (if he used PML to buy that house) while looking for the next buyer to sell it.

I’d love to be a resource for you and assist in any way I can as you continue your investment journey.

Talk to house hackers because that would be a great way to start, but you are also advanced with money so you may find smarter options that act more like index funds (syndications).

-Perhaps the cash flow "lining your pockets" continues for a few years.

Because they have no clue what so ever what there talking about, and there posting there feelings. 

Depending on how long it takes you to save up the amount, you might want to also allow for inflation on that amount for your continued savings.[2]   Read Rich Dad poor dad.[3]   Think about getting a second job - possibly a temporary job - save a 100% of the money.Just my 2 cents.