1) That is a little odd, the big drop over 6 months or so.....but you need to look at comps in the same neighborhood. I"m not sure which state you are in, but I can tell you in some parts of California, where I"m at, I wouldn"t even bat an eye at a drop like that. It can mean 1) it was overpriced to begin with, or 2) something"s wrong with the house and no one wants to touch it. Do your due diligence.
2) No, it doesn"t make much sense to offer less, maybe a little, but most of the value has been priced into the home at this point.A short sale is a pain in the ass to close.I can"t emphasize that enough. The big issue is that the home is being sold at a loss, which the bank has to eat, so they don"t necessarily have to agree with the closing price. They are also in no rush to sell the home. What can happen is 1) you put an offer in for $95k, 2) it goes into escrow, 3) MONTHS down the line (because, again, the bank is in no rush to sell the home) the bank decides the amount you offered isn"t enough, even though you and the "home owner" have already signed off on it. So you end up just wasting your time. I think a good estimate on the time from offer to close on a short sale home is about 6 months.
3) I would be really surprised, honestly, if you could get away with putting only 3.5% down. In fact, unless your finances are stellar, I would be suprised if you could get away with less than 20% down. The last thing a bank wants to do is give a loan to another guy who can"t afford the home. Putting down so little shows the world that you really can"t afford the home, and that any potential hit to your income (laid off, whatever), means the home goes back into foreclosure, since you don"t have much in the way of assets. Now, I know you meant FHA and not a bank per se, and I honestly never had to use FHA, but I would still be surprised if you could get a home loan with only 3.5% down. Definitely read the fine print and see what"s required of you to get such a good deal; I don"t think the government is looking to get screwed over by people either.
4) I"m not sure why you think you are being a dick.....is it because you two were planning on renting together? If you actually got a house, couldn"t you just rent a room out to him? Also, with his lease up in less than a month, don"t even think for a second you are going to get a loan and buy a house during that time. Again, you are looking at MONTHS to purchase a short-sale home.