It has been a few months since I have been in the area, but I would say that your best bet for a cash flowing property would be heading towards Hermitage on Route 70 or south of I40 heading towards Gladeville.

- background Condo is coming out of an Estate Sale and needs work - recent market activity, data from last month, similar units -  (1) Estate Sale - As-Is - listed for $129,000 - sold for $134,000 - (2) Well maintained /Updated - listed for $149,900 sold for $154,900 - admittedly might not be looking at this correctly in that (2) might not be relevant - thank you for helping meRemember, the idea for BRRRR is to get all your deposit back again once you Refinance. 

brokerage community is your best bet.

Get creative and cash out refinance, or get a HELOC, or HEL on my current property to free up between$13-$25K cash (at a price).

FHA is good due to the low down payment but the up front MI is very expensive.... in addition, you have to add .8 to your rate which is going to be your monthly MI so it will eat into your monthly profits; you cannot drop the MI, you would have to refinance to get rid of it. make sure you properly calculate the payment with all escrows and re-run you numbers...

An option is to use a HML or PML until you have more rental income and can refinance with a bank.

I am a little confused as to when/if I should refinance my home.

That value could go up or down depending on the specific factors of your market.If you apply for a refinance or other loan using your property for collateral, the bank will most likely order a new appraisal and base the loan on the current appraised value.

My wife and I recently did a cash-out refinance of our current home.

Consider refinance prior to moving out.