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?

You likely don't have the net worth, proper LLC management or proper separation of personal interests to make this an effective approach. there numerous BP threads you can search to get more insights. tldr - keep under personal name and get a good umbrella plan. 

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

There are down payment programs for duplexes, i have not searched or tried to do a 3-4 unit property. 

My initial plan had been to do something like Rent-to-Retirement or REI Nation- assuming that I'd be leaving money on the table to pay for their expertise, but hoping that I would learn through the process and develop the confidence to strike out on my own later. 

With careful planning and consistent effort, you can create a portfolio that aligns with your long-term goals.Good luck!

Do you meet with us routinely to be proactive and do planning?