1) An INFOPASS may or may not yield an immediate positive result, there's no guarantee. Only way to know is to give it a shot. Even if the outcome of the INFOPASS doesn't seem encouraging initially, the possibility of it bringing a case to the attention of whoever is in charge makes it worth it IMHO.
2) Early filing memo
http://www.uscis.gov/sites/default/files/USCIS/Laws/Memoranda/2013/August/DV-Related I-485 Applications .pdf
Other Considerations
The adjustment of status process for diversity visa winners must be completed by September 30 of the fiscal year the lottery pertains to. Visas cannot be carried over to the next fiscal year.
http://www.uscis.gov/green-card/oth...card-through-diversity-immigrant-visa-program
I am already in the United States. If selected, may I adjust my status with USCIS?
Yes, provided you are otherwise eligible to adjust status under the terms of Section 245 of the INA, you may apply to USCIS for adjustment of status to permanent resident.
You must ensure that USCIS can complete action on your case, including processing of any overseas spouse or children under 21 years of age, before September 30, 2016, since on that date your eligibility for the DV-2016 program expires. No visa numbers or adjustments of status for the DV-2016 program will be approved after midnight EDT on September 30, 2016, under any circumstances.
http://travel.state.gov/content/dam...Translations/DV_2016_Instructions_English.pdf
9 FAM 42.33 N5.2 Petition/Application Validity
Under INA 204(a)(1)(I)(ii)(II) (8 U.S.C. 1154(a)(1)(I)(ii)(II)), persons registered as DV immigrants are entitled to apply for visa issuance only during the fiscal year for which the application was submitted. The petition is valid until midnight of the last day of the fiscal year for which the petition was submitted. There is no carry- over of benefit into another year for persons who do not receive a visa during the fiscal year for which they registered.
http://www.state.gov/documents/organization/87838.pdf