We are in the business of low offers but that is a mind set and perception that can be overcome.  

There are literally millions of examples all around you of millionaires (sophisticated investors and financial neophytes alike) that were minted via the SD RE market.

However, if the perception is that schools and crime are getting worse, many will sell (even at a loss) to provide a good education for their children. 

Torey Chumbley sophisticated investors look at return of deployable equity.

I think it depends on the sophistication level of the PM you hire. 

I live 2 hours out of the city, so having my own property to book and stay in would provide a huge personal benefit in terms of being able to head into the city more without the stress or hotel fees.I guess I'm mostly hoping to hear if anyone has done this ... my initial concerns are (1) potential complexities with how the entity is set up/ business or otherwise/managing the books, (2) negative perception among vacationers in a complex or duplex format, and (3) finding a property manager that can manage some of the nuance of STR (such as cleanings) with the general maintenance of LTR.

https://www.biggerpockets.com/member-blogs/9232/55313-intro-to-section-8---your-perceptions-vs-my-realities

First post here but I've been incredibly impressed by the level of knowledge and sophistication of the community.   

Because of my use of property managers, don't need to track most property expenses in any sophisticated way.  

there some raising money laws out there...REG D maybe....and it does allow for you to raise money from a few non accredited investors...but i would stay away from doing this as you can get into some issues if the property goes south and it could be an issue as non accredited investors are not seen as sophisticated by IRS standards.