Doing a 75% 1st mortgage and 15% heloc or heloan would likely give you better cost of funds all around.If this is an investment property, you can do 80% cash out refi using NonQM loans such as DSCR loans, but at a higher cost/rate than if you stick with 75% loan to value. 

I would also never buy a short term rental in an HOA - it's just one more entity that can tell you what you can or cannot do. 

With one small exception on VA loans, there is no getting around the due on sale clause. 

Also, with a VA assumable, if the one assuming the loan is not a veteran, then the seller (veteran) entitlement will still be tied up in that property.

If you used a loan to rehab your property and find yourself in a difficult position, doing a straight refi (just paying off the old mortgage) will be easier than trying to pay off the original loan and take additional cash out.

Nashville is a fantastic market with strong rental demand and long-term growth potential.

We would rather buy in a higher class and have less cash flow/come out even and focus on appreciation and long term.

And you have to pay PMI for the life of the loan.

Tyler,Within my 20 years of experience as a landlord, if I had $150k and good credit, I’d focus on either flips for fast capital or rentals for long-term cash flow—trying both at once can slow you down.

Is the mid term rental business that you have a 'rental arbitrage' business?