1) Do you put the extra rent and deposit in escrow?

Of course it sounds good as extra income but as I am looking it does sound like a headache and not appraising well.

Now every week that passes, I'm paying extra to keep my rate in.

The goal is to have paid off properties to pay my parents extra income in retirement. 

I cannot see how build two, say, 1200 sq ft houses with two roofs, two foundations, presumable about 25-30% more windows and siding is going to be cheaper a duplex that might have a little extra fireblocking and soundproofing.Now, maybe your GC is thinking that detached homes tend to get higher rent than comparably sized and finished duplexes.  

If it brings enough to cover taxes, interest, legal fees and auction expenses, plus some extra, the people with redemption rights share the "extra." 

The extra cash will help because it shows that you have reserves, but you wont automatically get a sweetheart deal just because you have X amount of cash. 

Make extra money for flight school is good, but if you need extra money for flight school that tells me that you don't have a ton to invest into real estate right now.

I feel I can get similar rent for an oversized 2 bedroom with a finished office and storage room on the 3rd floor as I could with an extra bedroom.

Or their own file format, which opens their own software.I think I would have to pay extra for outgoing, however, over a certain number of outgoing faxes.