With this in mind, is it better to say I am interested in purchasing the house and then risk be ignored if they aren't interested, or simply say I wish to speak with them concerning a matter on the  house, for example, so they would need to call to find out what the issue is, and I can remove them from future efforts if they aren't interested?

Even if a bogus claim is made concerning your period of ownership, the costs to defend your ownership and the future owners' rights may fall on you. 

If you are really concerned about something bring out your contractor or other pro to have a look.

What other red lights should I be concerned about beside the standard DD requirements to purchase any PN?

I would like to be able to answer his concerns and I have some idea how but I would like for some of you to help me help him and help me.

I've been investing for a while and have really never been concerned with the implications of taxes due on sale.  

We do a lot of work in flood zones and from what I've heard regarding "stilts"(we call them pilings) is you're looking at 20-30k extra over a traditional slab with a crawl space....Most of our footings are within a couple feet of sea level so we've never needed pilings but if you're indeed that deep you defintiely can't pour a footing on top of muck.....The other concern is flood insurance - the lower your first floor elevation the higher the flood insurance - I'd imagine if your first floor is under 10' the insurance would be astronomical.....your best bet is to talk to an engineer, get a survey, and go from there.

If a tenant wants title coverage for a lease-hold interest, they buy it, generally not done, except in a long term lease where a tenant may have such concerns. 

The time and skills issue really does not concern the business itself, other than who is going to run/manage the business.

Hi Vince,It seems like you have done your math... are you unsure of taking the deal because you are concerned that it will not rent without a garage?