To locate the best short-term rental (STR) insurance for your Asheville property, consider must-have coverages such as dwelling, liability, loss of use, and additional living expenses.

Tres - For starters I would recommend you read "Short Term Rental, Long Term Wealth" by Avery Carl; You can find that book right here on BiggerPockets.

The inherited house is in a coastal town but I'm hesitant to do a short term rental as it needs quite a few updates (kitchen and bath) to make it desirable enough for a STR and I have no capital to do that.

In Philadelphia I would check with the seller or agent if they have a lease, if they do a standard eviction can take anywhere from 3-6 months to go through the great court system we have.

If you only need $30k fast and for a short term and aren't sensitive to cost, a private lender is probably your best option. 

Other real estate investors have also been very successful in areas such as Fayetteville and Moore County renting to military service members or even short term rentals supporting the PGA tour.

I just don't see a big enough difference between the RentRedi and all of the other free softwares to justify spending $9/month.Long story short: Why should I use RentRedi compared to the free options out there?

If you are going to wholesale the property, try not to blow smoke and say you need to have your partner come look at the property before closing - you are wasting the seller's time and many have been burned that way. 

I have interviewed several solo agents who work at exp/real and that is where I think they fall short.

If cash is the quest, just do a short term bridge loan.