You might consider engaging a local RE Agent to assist you with getting Leased up for the first time.

Best quote ever from Warren Buffett“Calling someone who trades actively in the market an investor is like calling someone who repeatedly engages in one-night stands a romantic.”For me REI is a definitely 'long term relationship' 

The second part of my question was more geared to the timing of engaging the different subs.

Now idea how that would be monitored but if they could find a way I bet they'd get a new level of engagement from those with a lot of experience.I know I have my own questions from time to time but don't really ask as there really isn't a forum designed for and checked by those who have been doing what I'm interested in discussing. 

That could be a great way to find and stay engaged with local investors, realtors and opportunities. http://www.biggerpockets.com/alertsYou can also search for other investors or brokers in your market and follow their journey on Bigger Pockets here: https://www.biggerpockets.com/search/usersAnd of course, be sure to subscribe to the podcast - so much great info there and also full of inspiration.

I've got a roadmap, but, as with all plans, I'm sure it will change as I learn, engage, and receive feedback.

That could be a great way to find and stay engaged with local investors, realtors and opportunities. http://www.biggerpockets.com/alertsYou can also search for other investors or brokers in your market and follow their journey on Bigger Pockets here: https://www.biggerpockets.com/search/usersBest of luck to you and look forward to following your success on BP!

Honestly, it's too bad that the operating part of your dad's business does not carry with it some residual value of some sort with regards to that commanding a sale price.My hunch would be that this would be far too risky to embark on as a first go of things.Especially, from what you're mentioning this may have a large impact on the quality of your dad's retirement.If you have the funds and can structure something, the place to start would be to engage with an A/E firm to get a cost estimate generated for a concept building like you're mentioning. 

Engage in intellectual discussions regarding it.

The proceeds from the sale of the original property must be held by a qualified intermediary escrow agent (the proceeds may not be received by the property owner wishing to engage in the 1031 exchange).Concerning you transfer of the property to LLC,  the IRS stated that an individual transferring replacement properties to a limited liability company (LLC) treated as a disregarded entity (i.e., SMLLC) does not violate the Section 1031(a)(1) requirement that the property be used in a trade or business or held for investment.So if your LLC is single member LLC, you can transfer( after you sort out Due on sale clause with your lender)