What should I invest in another rental property or a college savings plan?

I purchased a condo for $52,000 in 2000 and I can now sell it for about $127,000. I have been using it as a rental property but the management company is becoming a headache. I purchased it as a college investment for my 6 year old daughter. My question is would I be better off buying another rental property and not pay capital gains or would I be better off paying for College Illinois for each one of my 3 kids (under the age of 6). College Illinois costs $42,000 for a 4 year college tuition plan. I could pay for all 3 kids in full. I wouldn't have to pay for tuition in 2020 if I bought this plan. What's your opinion?

By the way, this isn't going to work as well as you hope. I'm assuming the property has been in your name all along.

$127-$52 (true gain) = 75,000 taxed at 15%= 11,250 in tax.
13K of depreciation recapture at 25% = 3250
So your additional tax bill is probably around 14500
That leaves you 112,500. You need $126 to fund all 3 years.

If you can come up with the other $13,500, great. (Keep in mind that you need to do a form 709 when you open the 529s because the gifts to fund them will be more than $12k.)

It is a little unclear as to who would manage the property if you continue in the rental market, consider putting a foot in both camps and finance the tuition for one at this point, you can then review your position annually, this will limit your exposure to tuition fee increases while taking advantage of any appreciation in real estate, the ability to nett off your fees against any capital gains at tax time also needs to be looked at... Just some thoughts. :-) Happy New Year .

your management should never be a headache id drop them and find ones u like in the area, then id secure my children's college they come first to me. after that invest and make money.

neither;
find a replacment mgt company
and re-fi the bldg
and take the excess cash and
buy
DELINQUENT TAX LIEN CERTIFICATES.........only in FEB of each year if your county sells them

or help people start companies
but put no more than $10k into
any one company--and
only in your community
and hire an atty to help you