You need to minimize upfront expenses because 100% of your investment is at risk and lost if the lot is not buildable.My favorite strategy is to locate the property and tie it up for usually no more than $100 for a period of 8-12 months, analyze it myself and if I believe it to have a chance at being buildable I create a permitting plan and market the property to other investors/builders willing to take on the permitting risk.  

Overall I think nationwide it’s getting very tough to get into the STR space and make money and the fact that a municipality can tank your business at any time calls for a strong back up plan from the start!

For example, I stay 99% occupied with my MTRs - the only vacancies are planned vacancies when I need a couple of days for a turnover.

Roads, water/sewer, city services, heck even just the planning for such is not a simplistic thing for all. 

Ofcourse I am planning to consult a lawyer first. 

If you're planning on only living there 1-2 years, rent may not change THAT much, so calculate what the rent would likely be right now for your side as well. 4.

We are planning to purchase a home and convert it into a community living space for people in recovery.

Cozy is notorious in holding your rent for over a week with the free plan.

The plan was to pay cash, refi out and use that to improve the property. 

You sell when it fits with your original business plan (targeted NOI is reached, timeline is reached, etc.). 3.