Doubt you'd get any repeat guests once they realize the water is brown from Rig City.

They like cookie cutter, by the book deals that fit their box. 

One of the good things about DSCR Lenders is that the guidelines and programs are different and not cookie-cutter 100% equivalent like conventional lenders that all must mirror the GSEs, etc.Most DSCR Lenders will have similar rates and terms and generally similar processes - so generally what will make the "best" one is the best one for your needs - I would focus on any specialties or niches - like short term rentals, if you do multifamily or mixed use, BRRRR Method or focus in on a specific market - find someone who specializes and has a good track record in that niche or area

Jury-rigging?

I think my insurance broker (AAA) was able to rig it somehow that one is considered my primary residence and the second a vacation home.

I have a client who does this model in oil fields in Texas and is making a killing doing it because they are so short in housing to place these oil rig workers.

It sounds like in your situation, the "DST" just layered in additional fees to process a 1031 exchange.The syndication game is rigged for the sponsor - and in some ways, it should be.

So my advice: understand your market and local regulations, avoid the average cookie cutter STR home, make your home STAND OUT and be aware of the significant upfront cost needed to do so, and absolutely hire a local PM company.

But I'm not sure that really matters (retail vs investor)I find that the whole (retail) RE market is rigged - against the buyer and the seller and favors the agent who expects to make thousands of $$ with little 'work'. 

Second, the brokers who perform these are often brokers with a lot of time on their hands, so the pool of brokers are the LEAST successful and newest brokersThird, the brokers are not educated in the proper METHODOLOGY to perform a valuation.Look, if you as a broker run some comps where the subject property is a SFR in a “cookie cutter” subdivision and the subjects age, style, amenities, condition, are similar to the comps being used, you’ve got a fair shot at a pretty accurate valuation.