If you plan to live in them, then property #2 doesn't sound too bad, except for the fact you state you don't have much money.

Not a bad way to start.

I wish I'd got started earlier (I'm 26 now), but people don't think it's a viable career option for a young person, and it's very easy to listen to the people saying 'It's too much to take on / It's a lot of money and if it goes bad you'll be in debt

This being our first time even contacting a seller, I was uneasy with being the one to bring the bad news.

The rents are (usually) substantially below market; there is deferred maintenance in the units; and the tenants have a Long Term bad habit of not following the terms of the rental agreement or LL/Tenant laws.By shaking things up immediately, they are put on notice to shape up or look elsewhere, and the sooner you get qualified tenants willing to follow the rules, the better.To be clear, I would NOT make such an offer to a tenant I put in, or at any time other than very soon after closing on a new rental.

Really bad, I think, to work with someone and get an approved short sale then back out.

Not bad...The packages we offered them started at $99 and topped out at $295 which included a free sign and or rider.

The bad thing about Section 8 is the yearly inspection that you must pass.

Why are Realtors such a bad thing, and is there anyway I can turn the tide?

Whats a bad area to one person seems to be a descent area to another.