I'll send you a private message to discuss the area further and how, if possible, I can bring any value to you or work together on something.

We're possibly (sorry for using the p-word) talking about 200 hours.

You could bring less down and possibly have a lower interest rate since you will be living there.

Quote from @Victor Yang:In addition, is it possible for me and my wife to gift 36k worth of equity per year of the house (under the annual exclusion limit) and therefore have none of the costs go towards the lifetime gift limit?

A quick call to your zoning attorney or architect should confirm that adding that garden unit is possible without needing any changes, exceptions, etc. under the current zoning.

If you can hire really good contractors to assist and a good manager/realtor-may be a possibility.

Possibly using mortgage/home equity loan on one unit we own to buy an extra one.3.

At the beginning, it may be difficult to get a more expensive property that will appreciate well and so your choice is go with the cheaper property and get cash flow until you can sell and upgrade, or wait for a really good deal which you may be waiting for quite a while and its possible that you will have spent so much time waiting that you could have purchased multiple cash flowing properties by the time you get a good appreciation deal that you can qualify for / refinance after the rehab. i know anyone can go out and get seller financing deals, HML, flip to build capital or whatever the case may be I am just saying sometimes those will be harder and could result in less deals overall. 

If a tenant causes a claim, why should the landlord's insurance pay - possibly resulting in an increase in premium or even a cancellation of the policy?

The best time to invest is always in the past, but that isn't possible, so the only thing you can do is start today.