@Kyle Carter just because a building has all section 8 tenants doesn’t necessarily mean that the cap rate will be higher on exit but it might attract a buyer(s) that are focused cashflow and not appreciation; therefore a lower price to juice the yield.One of my non negotiables if I were you would be to only buy in an area that is desirable.  

While the property is in a smaller town, it’s relatively close to a larger city, which I think adds a lot of potential for attracting both short-term guests and long-term tenants.The motel has fewer than 16 rooms, and the nightly rates are extremely competitive for the area.

The property has an amazing creek canyon (attached photo) is 5 miles from all the major attractions to Yosemite, and 7 miles from a lake.

Nonetheless, you can base the DSCR calculation on PadSplit rent (if there's a history of PadSplit income being produced) or short-mid-term market rent (an analysis done at the same time of appraisal).

Now, either I'm not posting in the right places of i.e Cragslist / BP etc or my ads aren't as well constructed as I think they would be to attract motivated sellers.

That being the next "big" city along the interstate but you are talking about smaller cities even further south than that.To attract more interest, a higher population and greater economic or job growth are necessary.

So at this point given the large amount of income that the wealth management company kicks off, this very nice profit from the real estate portfolio is looking less and less attractive every year especially considering the time and mental real estate it takes up for her and the tax consequences.

I'd love to hear others' opinions on this but I am a fan of making the house as attractive as you can to a potential buyer, even if that adds cost. 

This season often poses challenges in attracting tenants.

I realize this comes with the STR business but if I'm going to continue to use VRBO I need to find away to attract the "good" guests and minimize the bad ones.