Places like US Leads List sell their data at a premium because they are only letting 3 people per area use their info.  

With this loan you can avoid FHA's upfront Mortgage insurance premium (MIP) costs of 1.75% of the loan amount and the lifetime monthly MIP (~0.85% to 1%) as long as the loan is in force. 

IMO it seems like you're paying a premium for this guest house which may or may not actually provide you extra rental income.

You could do a 1031 exchange and get into a more premium property and handle the tax situation as well. 

Their cash contributions equate to about 20% equity each, but because you are putting in money AND all of the work, you have to get a premium on your equity.

It pays to discuss with a knowledgeable agent the potential risk, coverage, deductibles, etc and select what fits your business model.Others carriers are good too but the thing I don't like is they make you pick a policy term from 3, 6, 9, or 12 months and the premium is "fully earned" - meaning if you pick a 6 month policy and only need it 4 months you still owe the full 6 month term.

@Chris Lawrence - depending on which site you are on, you may be paying a 5% buyer premium on your purchase price.

I am getting 15-16% cap rate buy and holds from special people that I know, but most people are paying very heavy premiums.

As far as roofs go, we have enough hailstorms here that most new roofs are covered by insurance, and that cost to the insurance company is already baked in to the premium we pay.   3 of our houses have vinyl siding, so no painting required, just a power washing every couple of years. 

Our business strategy is to find stable properties with value add components, which are getting harder and harder to find without paying a premium.