Have more liquid that will be more attractive to any lender, conventional or HM.

In the second scenario, I am worried about the kinds of reckless tenants a college town attracts, and it would mean a longer commute to work for me. 

IMO, you are looking for easy and inexpensive deterrents that make the neighbor's house more attractive to crooks.

Just kind of cold now.Seeing as this is basically like a brand new high end home (might be a bit much for the area, but we did all the work ourselves and since we are gonna live here for at least a year or two, wanted it to look nice for us, and to attract a good quality tenant).

I do see that you are in San Diego and the price points there are less attractive than other markets, but you just have to decide to balance the ability to learn by doing self management for some time, or learn as much as you can about off-site management before taking the plunge into another market.  

Get over that, or you'll be taken advantage of all the time in this business.I'd keep the deposit, without question.I'm not sure on the grade of property you're dealing with here, or the tenants that you attract.

It makes the borrower attractive.  

If you know someone who has money in or could put money into a self-directed IRA, they could provide financing and you could offer an attractive rate, say 8%. 

We have a new tax bill that makes it less attractive to live in most of the NorthEast in addition to penalizing high-value mortgages.

I would eventually like to Cash out Refi after a few years of holding and roll into another but not sure how attractive the new mortgage will look.