good old days - setup a new server - huge 10MB MFM disks where we had to manually enter the bad sectors (written on paper on the back of the...

bitwise can be done - just on SQL Server you have a straight use of it on @options  https://docs.microsoft.com/en-us/sql/database-engine/configure-windows/configure-the-user-options-server-configuration-option?view=sql-server-2017 
or Active Directory on user/group account control field http://www.selfadsi.org/ads-attributes/user-userAccountControl.htm
the limit...

there is no particular place to install the drivers. some will default to a hardcoded path (normally C:\program files (or x86)) others will allow you to select where to do...

what have you found so far on google/documentation and what specific differences/relations between each pair have you questions about?

Just to list the options.
to use the old cardinality estimator (CE 70) the following options are available - final result is the same insofar as it relates to CE

on VS upgrade each package and solution to latest version.
some may not upgrade correctly which means they would not run at all on new server even if the inplace...

without going through all possible options (google can help there) why do you have the copy job on Windows Schedule instead of a SQL server job? 
It would be better...

if just moving the accounts to another OU within the same Domain it will not change the account SID so your servers will not be impacted.

openquery with truncate may work - if not create a stored proc on oracle that does the truncate for you and exec it through openquery

in the project file 
<DtsPackage FormatVersion="8">
in the package itself
DTS:LastModifiedProductVersion="15.0.0900.40"
  DTS:Name="PackageFormatVersion">8</DTS:Property>

this is with
Microsoft Visual Studio Professional 2017 Version 15.9.6
SQL Server Data Tools 15.1.61901.03220

possibly not the answer you wish for but what have you researched so far?

100 measures is not much - one of my "cubes" has 22 dimensions, 1 fact...

for tempdb there is nothing you can do.

if however you are also talking about having all permanent tables of a user on their own file(s) then it is...