That leads to an unnecessary conversation where people won't want to work with you because no one knows what a wholesaler is.

In the winters you can either remove them or insulate them.If you don't want to provide the AC units, I would have clear language in my lease about which windows they can be installed in, that they must be installed safely, can/can't be screwed into window panes, etc. etc.Ceiling fans are unnecessary effort in my opinion. 

You also could add any improvements since 2008 to the basis.A 1031 would benefit from the stepped up basis, but seems like an unnecessary complication for relatively small tax deferral(you have to pay it at some point).

Again, this is not a "fire and forget" type of investment strategy, because either you or him will have to educate yourself on a lot of real estate fundamentals, to avoid taking unnecessary losses.

Learning multiple things at once will only raise more question in your mind and keep you in a constint education fase(spending unnecessary money on coarse training etc..)third, once you know exactly what nitch interest you start with learning the lingo.

Especially if you're getting help to do it.That said if you don't plan to use your degree in the relevant field going into debt to do so seems like an unnecessary gamble. 

The are unnecessary for us anyway but in Jersey you may need them.

If they hesitate in answering a question or answer a question with rapid unnecessary chatter both indicate a person is lying.A second interview of the possibly 10%, maybe one 1 or 2  potential applicants, will result in a application being submitted for background and credit check but by this point you are most likely screening applicants that will easily pass.

If you determine that it is a need then go for it, but try to cut out unnecessary expenses early out.

Option #1 seems costly and unnecessary in my opinion.