Thanks I've been doing some homework on stuff and trying to figure out what the best plan is and basically from what I've learned is I just have to do it and learn from it.

@Andrzej Lipski could also be a great resource as he is doing a lot of wholesale stuff based on website SEO.

In your market, it misses the arrival of winter which has got to be a positive. 

Good stuff!

I don't think you'll go wrong either way; just coordinate enough time between the guest leaving and the guest arriving so you can ensure cleaning AND maintenance is done.

@Huggy Ford Bigger Pockets can be a helpful site but admittedly, we are usually only talking about residential stuff. 

Good stuff. 

Good stuff. 

I think the job would take a solid 3-4 days to complete, but the family doesn't really take vacations and I don't want to pay for a hotel for them to stay in during the time that job is done - even if they left, the amount of stuff to work around is troublesome.  

That said, I self-manage mine because most of that stuff I can do from my phone in 5 minutes a day, I just make sure I'm available to jump if/when some maintenance issue comes up.