That means you get your returns early.One measure of risk is Debt To Net Worth.

Be careful in Front Royal as Warren county has some stringent hoops to jump through before you can offer a short term rental

So my long winded question is, in making purchase decisions as a buy and hold investor should primary emphasis be placed on return metrics (ROI, cap rates, CoC, etc), with $/SF a secondary measure, or should it be a prerequisite that the $/SF price be at or below market in order to protect yourself in the case that you need to sell?

Everything is life is measurable and trackable.

@Greg Heden If the money is from a cash out refinance then you are likely paying higher than a 5% interest rate on the money, so you would be losing money if you just leave it in a MM account.ConC return is not a very good measure of a real estate investment (unless you are investing in class C/D and it sounds like you are not), as you mentioned you will also be getting tax benefits from depreciation and those benefits will be at a high rate because of your tax bracket, so I would try to calculate that and quantify it.

Another example in the link that Tom provided, the min bedroom size must be 110sqft, where as the IRC, Section 8 and my local municipality all require 70sqft with no less then 7' measurement in any direction.I 100% trust what Tom or @Mark Ainley tell you about properties, especially in the City of Chicago, they are the masters in that domain without a doubt. https://www.hunker.com/1371146...

The requirements for those two (which is where most loans end up) are very stringent and it sounds like you may not qualify.I'm also interested in some details about the deal - I haven't heard of any turnkey companies in Louisville and would be curious to see a local example.

FHA has their rules and lenders have ones that are more stringent. 

Keep in mind all measurements for storage are relative.

There are also a lot of people that are making a small return on Networth so that is not a really good measuring marker in my opinion.