No one ever need to enroll in any program or purchase any of our products in order to obtain a loan from us. 

Vacancy;  Rarely do properties stay fully occupied for ever.  

Smaller communities share the same expenses as a larger community and therefor do not cash flow as well.

You are on the right track searching for a commercial policy since the property is larger than a 4 unit. 

one basic reason is because if you ever needed to get that property back in your name or move it into a trust, etc, the transaction of removing it from the s Corp would be considered a sale and the s Corp would be liable for taxes from the gain, even though you’re moving it from an entity you own to yourself.

Do you ever pay your GCs extra when they get it done on time or early?

A hodge-podge of updates over 100+ years have left the houses with awkward spaces and outdated everything.The larger house is 1,625sqft duplex with a 3 bedroom unit on the first floor and 2 bedroom on the second floorThe small house is 1,150sqft duplex with 1 bedroom on the first floor and 1 bedroom on the second floorAsking price (FSBO) is around $240k for both (7 bedrooms total, 4 doors) but I'm fairly certain there is plenty of wiggle roomThese houses need *complete* remodels.

THIS is the best advice ever I can give you, have your number, and STICK to it.

But not as many venues can handle larger affairs of 200-300 guests, so there's less competition in that niche. - Do you have adequate parking?

AS I said it something that has been ingrained in every property Management Course I've ever taken as an Agent / Property Manager.Makes sense really, you want to get it rented as soon as practical.