If we then do a cash-out refinance (after seasoning) to pay back the HELOC, would PMI go away again (assuming we are below the 78 or 80% LTV threshold)?

More season investor please correct me if I am wrong.SFH up to 4-plex would be valued base on comps.

His company doesn't do STR, but they will do seasonal.   

Right now I’m in the phase of:-building credit + savings-wanting to develop my knowledge and skills I’m in the Memphis, TN area and would love to volunteer my time and skills with investors or seasoned people in real estate to grow my strengths.

Not as awesome as the first but more relevant.There you are a successful filthy rich investor making a lil day trip through the Caribbean seas on your fancy yacht when disaster struck.

If you are just rolling the purchase price and rehab costs with less than 6 months seasoning then you would be able to get traditional financing at a decent rate. 7.5 seems really high.

Bookings are down across the across the board for STRs this summer season.   

Season the property for 3-4 months, then do a 65-75% Cash-out ReFi. 

Also after 2019 tax season I will have two years of self employment to include on future loans.

I know that peak rental season is during summer, and most lease are one year long.