Re: Escape cold weather oil leak
First off, you can't go by someone else's ownership experience, as they all vary greatly. He might have problems that he managed to cause without knowing it. Highly unlikely that seals are bad within a year or two, but as mentioned, it can be possible as anything man made will fail eventually.
Factory tow packages are fail safe for the most part. The only problem I can see is if someone installed a fuse with a higher capacity by mistake, which can cause an overload and ultimately a fire if the fuse doesn't do it's job to begin with. If the dealer installed this 'box', as you mentioned, then they should fix the problem for him. If it was done at a no-name shop, anything can be possible.
If a block heater is faulty, you'll have coolant leaking, not oil. No engine heater than I know of heats the oil directly. All block heaters I've seen are in fact attached in place of a freeze plug, or similar hole alongside the engine block itself, not attached to the oil pan as warm oil will be just as effective in a frozen engine block - thus is why the block gets heated to make the coolant AND oil more effective to aid in starting the vehicle. If this is the part that the dealer wanted $750 for, they're on drugs. Block heaters can be had for $50-100 on most domestic vehicles and installed for similar money, or about an hours labour time. Looking at $250 TOTAL as the maximum with taxes, labour and parts.
Bearings in all new vehicles made in the last ten years are sealed. A bad wheel hub/bearing can leak grease out of it (not engine oil) if it's faulty, but unlikely in a two year old vehicle unless your friend uses it to climb up and down curbs all day long at 20mph. I guess I can say it doesn't make much sense to me either. The information he gave you is too vague to really speculate further.
I wouldn't put your friends Escape problems into consideration if you're interested in purchasing a similar vehicle. Escapes are great all purpose machines and can last a solid ten years before major problems, as with any other vehicle. Who's to say that your rich neighbour who plunked down $200K on a new lambo won't have problems with a bent driveshaft, transmission programming woes or any other problems. Meanwhile you can tell him you haven't had a single problem with your Escape. It's all in the maintenance, and how you drive the vehicle that makes parts last.
People that aren't capable, or aren't licensed to do the work can cause problems for you. If you buy new from a dealer, I'd take it back for service there at least for the duration of the warranty so they'll be more in line to fix any problems right away if one should arise. A service manager at an auto dealer KNOWS that service affects vehicle sales, and they won't jeopardize that.
'00 Durango R/T 360ci 290hp (modded); 138,500m
'06 Pontiac G6 GT 3.5L 220hp; 44,000m
'12 Chrysler 200 Limited 3.6L 283hp; 13,000m
'99 Taurus 3.0L 2V Vulcan 145hp; 154,300m - Traded
Amsoil in all vehicles!