. - I live in the city of Chicago, so for us there are plenty of areas / neighborhoods to choose from.

I would look for an equity partner. 20k isn't an ungodly amount of money and there are probably many people in your circle that would have money like that to invest, you just have to convince them and choose a good partner.

To be able to choose to go on vacation and not set a date when to go back home would most definitely be a great option. :)

I know if I choose to submit an offer later, I can add the contingency of right of refusal after inspection.

Connecticut has some of the highest property taxes in the nation, which will take a sizeable chunk of your cash-flow.Good luck with whatever you choose!

It required some basic maintenance to be move-in-ready;- We are planning to tear it down and rebuild and would rather hold off and get a mortgage when the house is built, so we can pull out more than if we had gotten a mortgage on just the purchase.Again, that's just one example of why someone might choose to pay cash, but it certainly made sense to us for this deal...

Most people don't choose to move at this time of year.

Choose to invest my money in a cashflowing property (let's say I can count on a 20% APR, and get taxed 50% on profit, so I end up with a net of 10% APR).2.

Just know that many people choose to pay their taxes each year.

I think that's why some people choose to own a portfolio of SFR's rather than a single multi.