You can set up each entity as a location and each property as classes, the downside will be more work (since you will need to fill out additional field for every transaction) and if you don't have a good system in place, it could end up in a mess.

What will the R-factor change be with the additional insulation?

Second, oh master architect, houses are not built out of Lego and you cannot just easily add a room or addition.

I guess I am just one of those basic lender types.put money out get a mortgage or deed of trust prom note.. lenders title policy and named additionally insured on the hazard insurance.I think your talking about an investment scheme.. :) of some sorts.. 

Also, an additional deal, if done right, could provide cash flow that he can allocate exclusively to his debt to help pay it down faster. 

To me, it's all about generating additional streams of income.

I want to start renting it out to create some more income, and am currently looking for an additional home in the area to do the same thing.

Since you will be on both the buy/sell side - you would then be paying 100% of the transfer tax.I suppose you would have to weight the cost of creating the LLC(which includes the additional cost to transfer it to an LLC) to the cost of the umbrella package and weighting the pros/cons of how each strategy will protect you.

Additionally, I have started to identify vacant properties in our area and started calculating practice deals so I can learn what metrics are important. 

Not to say that they will.As far as taxes and insurance, the one thing to make sure of is the mortgagee is the primary insured, and you as the additional insured, if that's what you want to do is to get your own policy.