If you already have some capital to start with, that puts you several steps ahead of most beginners.

I have that now, and the strides I've made in the past several years is astounding. 

I have been a flipper in San Diego for several years.

I have several realtors and I tell them that whoever calls me when I buy will also get the listing when I flip, so they are getting two deals in one!

I know several firefighters that do REI on the side. 

Tammy, I see several disadvantages to combining the properties into a single tax parcel.1) if held in separate entities, your liability is limited and you have significant asset protection.2) individually, you can borrow against the properties either through refinancing or Heloc.

Went many years with a beat up Honda, several Town Cars, 2 Toyota Sequoia's & finally Ram 1500's.

I cannot speak directly to STRs in the city of Asheville but I can tell you we have several astonishing properties listed on our site just outside of Asheville.Vacation Rentals in Clyde North Carolina

The current owner has owned for 30 yrs and needs to sell for health reasons. 

Basically you assume several exceedingly bad and increasingly unlikely scenarios and see what your finances would look like.For instance, look at what your numbers would be if 2,3 or 4 units went vacant and you had large capex expenses like a new roof.