It has a free plan that I think will meet my needs.  

Your situation is so difficult, and the best plan is to get financing before we need it. 

I have from time to time spoken with the city administrator, economic developer, & a person at building planning commission.

Educate yourself on the local market, network with other investors and agents, and always have a solid plan in place before making any investments.

Like any financing strategy, due diligence and proper financial planning are key to making it a successful solution for both parties. 

My question is: If the HOA changes the bylaws to ban smoking (which they plan to vote on), and the lease held by the smoking tenant only specifies no smoking "within the unit," is there any legal recourse for the smoking tenant?

@Drake BackmanBigger Pockets is a great place to find a tax strategist specializing in real estate taxation.A good real estate tax strategist can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding a tax  strategist specializing in real estate taxation, business taxation, financial planning and tax planning.Consider working with your tax strategist remotely to expand your options.I would also recommend looking for a tax strategist willing to work with you throughout the year.

You have to know the market before you build a plan and I don't think this market supports your intended plan.

I had a similar strategy with my first few house hacks: buy in great A & B Chicago neighborhoods....get by with minimum cash flow, and wait...What's your plan for the next purchase Michael?

Nathan is right regarding timelines, need to plan for 60 days for anything you want.