Do I have to wait a year or 2 when rents are increased to make the ARV higher in order to make refinancing worthwhile?

I'm a conservative investor, so these high cap rate cities are not something that I've been looking at due to the increased risk if we have a serious downturn. 2) Wait or buy now?

Tenants with increasing incomes. 

He bought the lot in 2014 for $44k and now wants $120k.House values in the neighborhood have increased 33 - 46% since 2013.

It’s not going to do you much good if you pull a bunch of equity out and increase your payment (likely with a higher interest rate) and the paymentand expenses are higher than what you’d receive for rent. 

This will increase your success rate at getting estimates and will be less time for you to meet them. 

Also, keep in mind that a condo comes with HOA fees that can increase in the future, eating into some or possibly all of your cash flow.

Once I retire in a week, and get the 457 money, it will give me roughly 80% of the down payment.I'll probably use a bit of my existing HELOC to get the rest of the down payment.I could ask my credit union about increasing my HELOC so I could use that to cover all of the down payment. 

For me the issue isn't so much using our equity as increasing the $ we have going to a larger mortgage each month, rather to savings/investment.

Being a renter, myself, for several years, I would not even consider month-to-month as I do not want the potential for moving expenses, rent increases, etc., if landlord decides to change the terms 2-3 months in.