@Curt Thomas - You already got your answer above from some smart people.Just curious are you asking from the tenants perspective or the landlord? 

We switched to being treated as an S-Corp for tax purposes around 5 years ago (later than we should have) and it was a really good choice, self-employment tax was trouncing us before that.

Are you saying it's not smart if you're a seller because people are charging not high enough interest?

But, I assume you are aware of that and obviously not concerned, since you thought it was smart to "purposely" choose your wording and post it as a headline, on a public website, for the world to see.

What makes it interesting is it has several parcels of land with the sale of the house which we could probably sell off the larger parcel for about 25-30% of the total purchase price.I know the basics of Section 121 but I'm trying to understand if there is a way to extract value from our equity position in our current house to make this a better choice than finding a straight rental.Current house Purchase $215K Current Value $280-290KOwe $160k 15 year mortgage at 2.75%Mortgage + Tax + Insur $1450Possible Rent $1800-2000Possible Live-In FlipPurchase $300KRepairs ~$20k-40kARV $325-350k (excluding land to be sold off)Land Parcel Value to be sold off $80k-100kI would love to hear your creative thoughts on this situation and how I can optimize.Thanks!

Your trying to leverage up or out and that's the smart thing to do.  

I am a Marine as well, your brother is a smart man lol  

Also look at the monthly bills for electric and heating....and if there is a pool(s) the water evaporation replacement costs.Does it have 100 year old chimneys that are unusable and crumbling, needing expensive scaffolding re-pointing or removal.I'm just pointing out there are LARGE dollar outlays beyond normal for these big Trophy Homes that it would be smart to budget for monthly.Do you intend to ride a lawnmower and cut the grass yourself or pay for it--etc...

In my gut there was something off but maybe i was scared or nervous to make the wrong choice?

@Julie Verardi  are they obligated to shovel and get a $40 discount each time it snows or do they have a choice to shovel or not?