I am new to BiggerPockets but I have been following Josh and Brandon via YouTube for about a year now. 

Side notes:Right now I am getting the impression that Pilsen is the biggest opportunity neighborhood to find a multi unit within FHA limits and still be close to the Loop via public transport.

For title insurance, call the closing attorneyMortgage payments-This is not fixed, it is variable, there are lots of calculators on the internet such as http://www.quickenloans.com/mortgage-calculatorProperty taxes- Also varies per property, look up the assessed value on each property via a link from the town website, and then the town tax rate should be listed on the town website. 

You can go under contract online via docu sign.

They have some upcoming projects that will also need to be funded via a special assessment.

Banks can't get out of their own way in order to close faster than 30 days.This is quite true, but what is somewhat ironic and comical is that the bank as seller will find an offer with a short closing time to be a stronger offer than the offer with a longer closing time; then once under agreement the settlement will get extended as needed by bank asking for amendment to the agreement via an addendum.

I'd appreciate it if you could help me gauge an understanding via a answering a few questions for me.1) Have you worked with general Contractors help"beautify" a house to fetch a higher asking price.Basic quick rather inexpensive upgrades to add value.

San Diego has some very distinct neighborhood boundaries that aren't apparent if you aren't intimately familiar with the area.  

Below I have compared 2 examples of selling traditionally with a Realtor at 6% commisions (which it may be less as it is negotiable) vs selling with opendoor or similar service.Comparing Opendoor to a Traditional Sale with a Realtor$400,000 Home via OpendoorHome Value: $400,000Sales Price: $375,000Charge 12%: $45,000Commissions 7%: $26,250Total Costs via Opendoor: $71,250Net Proceeds to Owner: $303,750$400,000 Home via a RealtorHome Value: $400,000Sales Price: $400,000Traditional Closing Costs 3%: $12,000Commissions 6%: $24,000Total Costs via a Realtor: $36,000Net Proceeds to Owner: $364,000In this Example Selling with a Realtor will save you $60,250!!!

Yes market seems much different these days on the acquisition side via regular chanels MLS etc. but the upside is if you are able to find right deals ARV's-retail market sales and profit margins are great.