I would advise at the very least actively looking into it and seeing what your options are and if something is appealing enough using a 1031 to put into another, larger property with a ton of potential. 

They will look appealing from the outside.

By tax card I assume you mean tax appraisal and the answer would be the only thing you should really look at is the tax rate, any special assessments, the recorded owner, and if the appraisal is too high and in need of an appeal.  

It appeals to seniors with small lots and upscale homes, however, the homes are large (built during the McMansion era) and require upkeep. 

Now, the assessed value is very rarely correct (which is why you should always appeal taxes), so this doesn't mean the building is actually worth that amount.

One smaller note, Cook County just reassessed taxes and it's a pretty big bump (at least on my properties before I go to appeal). 

Thats 'very appealing when people are fighting the cold in the northeast and midwest, and it's golfing weather in Phoenix.

If renting then I’d venture to go more affordable as a renter won’t likely care about siding color.If you’re planning to sell then curb appeal and standing out makes sense.

One thing I also agree with Grant Cardone on is that you want to be in a market that has some appeal and exposure to the rich, especially the international ultra wealthy. 

I live in Georgia and have found a few off market parks and some on market that are appealing.