Out of State BR(STR)RR Help

[Jeremy Absher]

As a new investor (I'm a high school teacher with two boys) I'm looking for advice/help on investing out of state on my first BRRRR; however, as the title suggests instead of a traditional long term rental I'm wanting to utilize it as a short term rental on platforms like Airbnb and VRBO. I have 4+ years renting out my primary home as a STR so I know the ins and out of the STR business.

I'm looking to purchase a property under $50k with cash, renovate it, furnish it and list it on Airbnb/VRBO and then refinance to get my initial investment out and pay back whoever I borrow the initial money from (I'll probably be putting in around $10-$20k myself).

So far the two markets that interest me the most are the Valdosta, GA market (closer to home ~3.5 hours away) and the Chicago market. They both have inventory of homes below $50k, have a good market for STR as well as a good rent to value ratio for LTR as a fall back plan if something doesn't work out for the STR market.

I'm looking for a good realtor in the Valdosta and Chicago market and/or someone who has knowledge of either of those markets who can steer me away from the war zones and to the areas I should be looking. 

I'm also looking for advice on the best place to look for $40-$50k that is not a traditional bank loan since I'm only wanting to close once after the renovation when I refinance with the bank and do a cash out refinance.

Thanks in advance for any help!