I cant estimate ARV so I figure I am just watching at this point.

He said when I accumulate more, we can buy a commercial policy.I plan on opening two accounts (one for condo, one for the 12) as there will be two management companies accessing the accounts.  

However my contract is set up with the $4000 down and my key worry they accumulate $100 a month towards their down payment.

Scott The Book on Flipping Houses, The Book on Estimating ReHab Costs http://www.biggerpockets.com/flippingbookConsider checking out HUD homes for small multi's owner occupied gets first crack.

65th Congress  should be okay area3/2 or 4/1 rent estimating without viewing property $1,000 through $1,100 via traditional tenantsor more importantly section 8Definitely asked your buyer agent to run cma for this propertyGood luck

Scott The Book on Flipping Houses, The Book on Estimating ReHab Costs http://www.biggerpockets.com/flippingbookGood read The Real Estate Agent’s Ultimate Guide to Working with Investors http://www.biggerpockets.com/renewsblog/2013/08/24/real-estate-agents-working-with-investors/Download BP’s newest book here some good due diligence in Chapter 10.

Based on your 6 month timetable estimate, thus will put you squarely in selling thus autumn.

I'm also trying to be conservative with my expenses and estimated rents, so I wouldn't be surprised to end up closer to the $200/mo area.

I had to put all my reserves into the property and had nothing left to catch up the arrears that had accumulated. 

He was fine with that seeing how it only took about 30 minutes to give me a good estimate.