Would it make more sense to move the money we make from selling to a different property that could potentially increase our cash flow? 

You want enough so that a potential law suit would go away if the insurance paid out.Best thing is to highly maintain your property and treat guests with respect so that no one would ever want to sue you.

I know that this is a big risk property but I believe that it has the potential for high return if I can get all of this permitting and renovation work figured out on the front end.I'm just looking for any advice on how to cover myself on the front end prior to making an offer and how to expedite the work so that I can get renters in and start recouping on the investment as soon as possible.

I know the potential of already having the deal under our belt prior to his arrival. 

I am potentially looking into getting a trailer at the begining of the year getting a trailer that may need some work to rent out.

Additionally, the price point is still cheap enough to find the 1% rule and positive cash flow and there's amazing appreciation potential.

The BRRRR method (Buy, Rehab, Rent, Refinance, Repeat) could also be a great strategy to recycle your capital.To find deals, try direct mail campaigns targeting absentee owners or distressed properties, or go driving for dollars in neighborhoods with strong rental potential.

Or is it one of those things that would potentially pay off in 5-10 years?

Cash Flow Potential: Rental income from real estate held in an SDIRA flows directly back into the account, allowing you to reinvest and compound your wealth tax-advantaged.

These areas often have 3/2 SFHs in your range, with decent BRRRR potential.