@Greg StrunakA good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

Focus on what the rents will look like post-renovation with 4 units instead of 2, and have a clear game plan for refinancing to pull your capital back out. 

What would you do with your current residence if you planned on living in the new one to get an FHA loan?

But as often happens, a certain percentage of my investments “go off the rails”, in other words don’t proceed as planned.  

Unlikely.The backup plan is to have a strong lease.

I plan to invest into smaller multi-family 2-5 unit turnkey properties.

Below are some actionable steps I plan to take after identifying a market:- find a rock star agent by referral and/or calling brokerages and asking to connect with their top producing agents- find a rock star contractor by referral and/or yelp- have control over construction by setting per diems to incentivize contractor to finish the project on time, within budget, and with good quality- leverage my rock star agent's time to check up on the construction process (checks and balances)- hire independent handymen/inspectors to check up on the construction process for a flat fee (checks and balances) There's competition everywhere, you won't escape that in any market. 

It's in a rural town so I'm also worried that demand might not be as high as in more densely populated areas.I'm planning to call local banks this week to understand financing options and contact some contractors who might be interested in building additional units. 

Some agents might offer flexibility, like a non-exclusive agreement, especially if you’re upfront about your plans to explore multiple opportunities.

Through your local bank that you are using, are you reapplying for each new home for a seperate construction loan or are you setup as a credit line with them and just submit a new budget for each new home 7 mil credit line  ... new budget for each plan that has been pre appraised in the MAI at the beginning of the project.. they did have to update the Mai last summer but again did it at their cost not mine.. banks have to paper their files.. even though we are selling the same floor plans for 100k more per plan than the original numbers came it at and bank has been paid and has all the closing statements showing this data..