You need to think about your investment in terms of ROI (Return on investment).  

My long term REI goal is to generate $120k per year in passive income (this number is always going up to account for inflation).

Hey Michelle, what I would say is to keep calling that list.I like pulling expired leads, pre- foreclosures , and probates at the moment so I can do creative deals!

A per bed, mid term approach seems like it would be the best approach in its current state.

At this point, a good real estate agent can negotiate the selling terms of the property and get a contract in place.

It's tough to say with certainty and it a lot of success in the MTR market hinges upon operating ability, property layout, understanding your clientele and ability to adjust to the market.This article does flag some cities that are good for MTRs: https://www.stessa.com/blog/hot-spots-medium-term-rentals/

The lady said it's like Section 8 but for a limited term of one year. 

Hello Group I have a short term rental in the Santa Cruz area that I am looking to get homeowner's insurance on. 

I trusted this agent because she was recommended to me by one of the MTR gurus/book writers as a high professional investor-friendly agent.I had planned to implement a mid-term rental (monthly) strategy, but I cannot do so due to HOA restrictions and high insurance costs.

I agree to repay any duplicative assistance as directed by the Agency.Nothing in this Agreement precludes the owner/agent from using any and all remedies available under law, including the institution of eviction proceedings against the Applicant, if the Applicant fails to pay any future rent due after the date of this award or otherwise violates the terms of tenancy.I reached out to my lawyer, who told me rudely that he wasnt contracted to advise on this, and i offered to pay, but never heard back.