After a Valentines purchase as well as a couple others, I was able to convince him this was a good move.

Patricia- If you are looking into professional management, one of the first questions I would ask is about their cancelation policies as well as reading their reviews.

And you can be a landlord that gets a very poor return because they haven't utilized their space well by changing the layout.

I ended up signing with them as well - 3 months in to the lease so far and it's going well.

I want to be a investor buying and holding as well as fix an flips.

You will be obligated to modify your home insurance once you leave, regardless of whether you self-manage or not and this would apply to Scenario 2 as well - for any property you don't occupy yourself.3. 

The contractor is responsible for paying their subs so it would be a breach of contract between flipper and his GC if it was written well. 

@Hector Lewis - The decision ultimately depends on your current cash reserves relative to your financial needs, as well as your willingness to reinvest for potential appreciation.

Price range seems to be so fluid from what I'm seeing - as I'm sure you well know this but a home in one town might be $20,000/$30,000 variation in another.

You might be able to get away with shopping and nickel and diming for a few loans, but once you start to scale, you will see how valuable having a lending partnership with someone that is well-versed in all mortgage products is.