Then possibly get hit with a $100k special assessment while you have it?

Good morning,Can anyone recommend a reputable general contractor who can specialize in rehabbing a multi family in the chicago land area.

If you go into multiple units eventually it may be the easy button to do that.We use Bizcor which specializes in STR sites, but it may be overkill again as I think they cater to PM's.

I would try to find a great agent first that specializes with investors 

Specializing in how to use your investment accounts to invest.

Instead of taking bits and pieces of everyone's information which will vary greatly by municipality, consult with a local contractor who specializes in basement conversions.

I work for a full-service brokerage that specializes in investing, particularly in working with non-US residents.

Can anyone recommend a good accountant that specializes in STR tax strategies for W2 earners?

It's a great way to get started specially if you have a solid long-term plan.

I recommend finding a financial planner who specializes in real estate taxation, tax planning and financial planning.You may want to consider working with your financial planner remotely to expand your options.I would also recommend looking for a financial planner willing to work with you throughout the year.