I only use it 4-5 months each year so I would consider renting it out furnished, with heat, ac, internet, and semi-upgraded cable for $3200 per month.
Since you plan to be a long-term investor and clearly have 4k/month (since you are paying that in rent now) to spend housing monthly, based on the small amount of information we have about your situation, buying seems to be the best option for you.
As has been said here, it is a buyer's market, interest rates are incredibly low (if you plan to finance a purchase), and if you are a highly qualified buyer, you are likely to get a good price.
Additionally, you should consider the "other" benefits of home ownership - the intangible ones.
You should definitely speak with a Gold Coast real estate agent and a mortgage expert about your financing options and what you are looking for. You may also want to speak with your accountant about the tax benefits of home ownership.
Americorp Real Estate
Brokers Associate, e-PRO
If necessity is the mother of invention you may find that your necessity is to purchase. Why? Inventory that responds to your need time wise is in all likelihood short term or vacation rentals. From my experience in this category pricing that responds to your cap in the area you desire will be limited mainly to one bedroom condos. Two bed condos will price higher and, if you are able to find a place that works for you, will vary year by year and may vary month by month. Having said this your timeline is somewhat meaningless if your own because your ability to rent will be curtailed. One respondent indicated many buildings will not allow leases of less than six months. True. Many more only allow one year leases and some have limitations as to how often you can rent.
Is it a good time to buy in the area you desire? In a word, very good. Actually, that's two words. I suppose because a single word doesn't truly reflect how positive the market it is for buyers now. And having said this, find an agent with whom you relate who will shoot straight with you, help you sift through the dung to find the diamonds. If that's me, great. If someone else, best of luck. There's plenty to choose from.
The Real Estate Lounge Chicago with @properties
Expertise in Negotiation, Buyers' Representation, and Luxury Home Marketing
Over $100 Million Dollars of Personally Negotiated Transactions
Many buildings do not allow rentals for less than 6mo or 1 year so you need to check before you buy.
If you rent each year you will probably pay 3K or more for a furnished unit and you will probably be in a different building every year and will have to deal with finding something each year. Some buildings require a 6mo minimum for furnished rentals. Those that do not often want more $$$ to compensate although it might depend on what time of the year you need it. Winter is easier, Spring/Summer is harder.
You should probably have an agent send you the options for both rent and buy to see what you think.
Call me if you need assistance.
With low interest rates and amazing short sale and foreclosure opportunities if you can buy its a great time to load up on real estate!
If you would like to discuss search parameters give me a call or send an email.
Best of luck!
Your Real Friend in Chicago Real Estate