As others pointed out, the falling shingles can be an issue when removing the existing roof but it really should be minimal to the inside.  

Do flat fee property managers exist (I understand I would pay additional for large maintenance if the cost is above X)?

Do flat fee property managers exist (I understand I would pay additional for large maintenance if the cost is above X)?

If not, can they be sold subject 2 while keeping the existing blanket loan in place?

Both tear downs and adding Sq. ft. on too the existing structures.

@Christian Bors I like the idea of snowballing the cash-flow giving me the option of using that cash-flow elsewhere or accelerating the pay down of the existing mortgages (although i am getting quoted 3.875 on a 30 yr fixed now) thus money is still cheap.

They may be more open to being a little more creative or offering better terms on a cash out re-fi on your existing portfolio, particularly if you are willing to move all of your business over to them.

.#3 Atrociously Expensive. is the one that draws the greatest ire, and I'm really not sure why since the entire BP boards existence is predicated on the notion of an industry that specializes in selling at a profit, or servicing for fees.

Today's existing issue should be resolved before adding features.

There aren't a lot of them, and you have to be patient, but they do exist.