Shop around and let them know to give you their most competitive bid because you will be shopping.

If the market is a competitive one, like mine is, what is more important is having the lender who can and will close the deal seamlessly, and on time.  

And this is absolutely what I'll do if I end up in competition, but I sort of feel that even at $149,500 that's not a bad deal so would they really go a lot lower?

"Nothing quite in this area" is probably a bad sign - I know it may seem like a lack of other short-term rentals means a lack of competition, but it may also mean a lack of demand.

SD is very competitive and holding for appreciation while likely taking a loss in the short term is not the strategy I am trying to pursue at the moment.

Its also easy to feel defeated in a sellers market where competition is stiff and obvious discounts are few.

Best way is to obtain authorizations for release of credit, tax returns, assets and liabilities, then send copies or get several originals to use, mail them  and obtain information directly from the source, this cuts out the chance of fraudulent statements.You also need to underwrite the type of business, what hazards are present, toxics, fire, insurance coverage, competition with other tenants, traffic counts, environmental laws applicable to them as well as your infrastructure being sufficient for tha use.....electrical, plumbing, traps, fire codes, etc. 

If I do not hire a PM my plan is to leverage a local handyman that I connected with for repairs and maintenance and his wife actually runs a 140-unit nearby, so she offered to help me on the leasing front (meet prospective tenants for showings, etc.).I have a couple of PM's that were referred to me that seem to have some competitive pricing. 

Frankly, you can pay to learn everything at a fraction of the price.

It's tough but with the volatility in the market it's not worth it to me thinking I have one amount, getting my offer accepted, and then come to find out the market falls and I have a fraction of it.