Thinking about buying a second home. Best area?

[Paige65]

I'm assuming you didn't post in the Chicago suburbs for financial advice so I won't include it. If it were me, I'd buy a two bedroom condo in the city. For three to four times a year, I probably would not buy a SF home anywhere because I would personally hate paying the taxes on it - regardless of my ability to pay. We have a second property, and if we aren't using it a lot, when property tax time roles around I feel guilty for not using it more. Essentially, throwing money away for little benefit.

I do know a handful of people that have second places in the city, but they go at least a couple of weekends a month (as they only live in the suburbs).

[chicagoliz]

This is my fantasy, but I could never afford it. If were in a position to do it, I'd be able to pay condo fees -- I'd want someone taking care of the building, etc., and know that it was safe while I wasn't there. So, I'd try for something in one of the buildings in Lincoln Park. Maybe Loop/South Loop if I wanted something less expensive. (Although again, if I could afford a Chicago vacation home, I'd probably want it in the Lincoln Park area.)

[chicagoliz]

Originally Posted by chet everett

....FLORIDA is place that LOTS of people routinely list as a having nice enough weather to go there solely for that reason. You can hang out at a public beach, wander around in everglades or just go stroll around in flip flops while friends back home are wearing parkas.

While I have been in Dallas when it is VERY hot, like over a 100, and I can understand wanting to get out of there, but probably not to some random townhouse, cheap condo or single family home that might be miles from anything remotely entertaining.

I agree that there may be some "lifestyle" advantages of being able to jump on place an be outta Dallas but if the single family home has a yard that is overgrown (or burned out and brown...) it ain't gonna be a relaxing getaway like showing up at a hotel. it is gonna be a hassle...

The advice about doing without a mortgage is probably sound, but as many people have found, even without a mortgage taxes need to be paid, insurance has to be current, maintenance needs to be scheduled and all the assets you have tied up in an illiquid piece of real property are money that is NOT doing anything to really build your wealth.

Unless the OP is staying in some REALLY pricey hotels they'd really need to spend much more than 3-4 times a year in Chicago before this is feasible.

This. Florida is also SIGNIFICANTLY cheaper than Chicago. It's much more feasible to have a vacation home down there.

[GoCUBS1]

Originally Posted by pinipig523

Where should I be looking? What would you recommend for me?

Do you have a budget? Since you are from the area, what towns/areas are you drawn to? I have other homes and the one thing I require is that the HOA allows for renters, which keeps my options open.