From a financing perspective you won't be able to get bank debt unless you or a partner has to net worth to secure one - you will be going the hard money route (aka expensive) but even then we would look at the experience quite seriously and you will need a fat deal.I think people underestimate the permitting process, time, fees, and qualified team you need to actually build a brand new house - and that is just from a permit perspective.

We have had some pretty fat wholesales and a good buyer won't care as long as you are leaving lots of meat on the bone for them as well.

A lawyer who sees that set up would only take the case with a big ole fat retainer. 

If that is the case, you may want to get a fat, not 1 or 2 but multi-mil, umbrella policy to save you some money instead of upgrading each of your properties' liability coverage.FYI, a while ago, numerous Bay Area restaurants were hit by lawsuit from a lawyer, https://www.cbsnews.com/sanfra... 

You don’t ask Brad Pitt what it’s like to be ugly, you don’t ask the fat guy for weight loss advice, you don’t ask someone living pay check to pay check for financial advice and you don’t ask someone who’s lunch money is dependent on commissioning your wallet what you should invest in.

Also I do believe there was a verbal contract in this case but it may be a toss up if lawyers were to get involved and it doesn’t seem that they want this to happen.If the Sibling did not report the money the sister was paying on the mortgage but was taking all of the tax breaks for owning the property I believe the IRS would be sending her a big fat bill and possible more.

There is reason for "pigs get fat, hogs get slaughtered". 

Not a fat at the moment.

The main house is a 4/2 2500 sq ft that was built in 1900 and needs to be updated before it could be rented it has a newer roof and stays dry but needs new windows plumbing and electrical as well as some foundation work so it’s on the back burner for now.

Your return air has no effect on the burner section of a furnace, every furnace has an induced motor for this.